# Supplementary Information (SI) for RSC Advances.
# 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_dv_cf23
_database_code_depnum_ccdc_archive 'CCDC 2415596'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2025-01-08 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2024-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   9.4298(3)
_cell_length_b                   17.4070(7)
_cell_length_c                   9.4334(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.2680(10)
_cell_angle_gamma                90
_cell_volume                     1539.18(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0966 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.9348.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17238
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.340
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                2723
_reflns_number_total             3314
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.055
_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)+(0.0672P)²+0.1853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C13(H13)
1.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
1.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
1.e :
 C11(H11)
;
_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
C1 C 0.6969(3) 0.40587(16) 0.6210(3) 0.0484(6) Uani 1 1 d . . . . .
C2 C 0.5983(3) 0.46419(16) 0.6201(3) 0.0513(7) Uani 1 1 d . . . . .
H2 H 0.607641 0.501406 0.691236 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4855(3) 0.46757(15) 0.5137(3) 0.0481(6) Uani 1 1 d . . . . .
H3 H 0.419950 0.507434 0.514720 0.058 Uiso 1 1 calc R U . . .
C4 C 0.4667(3) 0.41314(13) 0.4048(3) 0.0396(5) Uani 1 1 d . . . . .
C5 C 0.5694(3) 0.35406(13) 0.4060(3) 0.0389(5) Uani 1 1 d . . . . .
C6 C 0.6808(3) 0.35185(15) 0.5125(3) 0.0455(6) Uani 1 1 d . . . . .
H6 H 0.747940 0.312742 0.511740 0.055 Uiso 1 1 calc R U . . .
N7 N 0.3538(2) 0.41710(13) 0.2947(2) 0.0485(5) Uani 1 1 d . . . . .
C8 C 0.3195(3) 0.34682(18) 0.2152(4) 0.0573(7) Uani 1 1 d . . . . .
H8A H 0.250772 0.357650 0.133476 0.069 Uiso 1 1 calc R U . . .
H8B H 0.277308 0.309938 0.275354 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2288(3) 0.46290(18) 0.3182(4) 0.0594(8) Uani 1 1 d . . . . .
H9A H 0.166669 0.466260 0.229448 0.071 Uiso 1 1 calc R U . . .
H9B H 0.259504 0.514580 0.344993 0.071 Uiso 1 1 calc R U . . .
C10 C 0.1465(3) 0.43155(19) 0.4297(4) 0.0582(7) Uani 1 1 d . . . . .
C11 C 0.0815(4) 0.4070(2) 0.5190(5) 0.0727(9) Uani 1 1 d . . . . .
H11 H 0.030070 0.387482 0.589594 0.087 Uiso 1 1 calc R U . . .
C12 C 0.4543(3) 0.31353(19) 0.1656(3) 0.0546(7) Uani 1 1 d . . . . .
H12A H 0.430876 0.269060 0.105658 0.065 Uiso 1 1 calc R U . . .
H12B H 0.499548 0.351452 0.110111 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5551(3) 0.29044(15) 0.2946(3) 0.0435(6) Uani 1 1 d . . . . .
H13 H 0.512968 0.245934 0.337855 0.052 Uiso 1 1 calc R U . . .
N14 N 0.6935(3) 0.26661(13) 0.2552(3) 0.0517(6) Uani 1 1 d . . . . .
C15 C 0.7820(4) 0.3145(2) 0.1744(4) 0.0776(10) Uani 1 1 d . . . . .
H15A H 0.799168 0.364078 0.219801 0.093 Uiso 1 1 calc R U . . .
H15B H 0.737171 0.322277 0.077921 0.093 Uiso 1 1 calc R U . . .
C16 C 0.9156(6) 0.2711(4) 0.1740(9) 0.134(2) Uani 1 1 d . . . . .
H16A H 0.937653 0.263773 0.076911 0.161 Uiso 1 1 calc R U . . .
H16B H 0.993497 0.299277 0.225981 0.161 Uiso 1 1 calc R U . . .
C17 C 0.8980(5) 0.1968(3) 0.2418(5) 0.0961(16) Uani 1 1 d . . . . .
H17A H 0.973422 0.188429 0.318699 0.115 Uiso 1 1 calc R U . . .
H17B H 0.900340 0.155538 0.172952 0.115 Uiso 1 1 calc R U . . .
C18 C 0.7547(4) 0.20003(19) 0.2985(3) 0.0613(8) Uani 1 1 d . . . . .
O19 O 0.8108(2) 0.39370(15) 0.7226(2) 0.0693(6) Uani 1 1 d . . . . .
O20 O 0.7017(3) 0.15156(14) 0.3704(3) 0.0822(8) Uani 1 1 d . . . . .
C21 C 0.8366(6) 0.4475(3) 0.8338(4) 0.0906(13) Uani 1 1 d . . . . .
H21A H 0.848893 0.497607 0.794276 0.136 Uiso 1 1 calc R U . . .
H21B H 0.921387 0.433389 0.893765 0.136 Uiso 1 1 calc R U . . .
H21C H 0.757007 0.448329 0.889189 0.136 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
C1 C2 1.376(4) . ?
C1 C6 1.386(4) . ?
C1 O19 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(4) . ?
C4 C5 1.411(3) . ?
C4 N7 1.406(3) . ?
C5 C6 1.373(4) . ?
C5 C13 1.522(3) . ?
C6 H6 0.9300 . ?
N7 C8 1.453(4) . ?
N7 C9 1.460(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C12 1.517(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.477(5) . ?
C10 C11 1.175(5) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.514(4) . ?
C13 H13 0.9800 . ?
C13 N14 1.456(3) . ?
N14 C15 1.453(4) . ?
N14 C18 1.339(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.468(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.460(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.508(6) . ?
C18 O20 1.223(4) . ?
O19 C21 1.408(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 C6 118.5(3) . . ?
O19 C1 C2 126.4(2) . . ?
O19 C1 C6 115.1(2) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.1(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 N7 122.4(2) . . ?
N7 C4 C5 120.3(2) . . ?
C4 C5 C13 121.1(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 C13 119.2(2) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.3(2) . . ?
C5 C6 H6 118.8 . . ?
C4 N7 C8 116.6(2) . . ?
C4 N7 C9 118.3(2) . . ?
C8 N7 C9 113.6(3) . . ?
N7 C8 H8A 109.8 . . ?
N7 C8 H8B 109.8 . . ?
N7 C8 C12 109.5(2) . . ?
H8A C8 H8B 108.2 . . ?
C12 C8 H8A 109.8 . . ?
C12 C8 H8B 109.8 . . ?
N7 C9 H9A 108.8 . . ?
N7 C9 H9B 108.8 . . ?
N7 C9 C10 113.7(2) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 179.6(4) . . ?
C10 C11 H11 180.0 . . ?
C8 C12 H12A 109.9 . . ?
C8 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 C8 109.1(2) . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C5 C13 H13 107.3 . . ?
C12 C13 C5 111.2(2) . . ?
C12 C13 H13 107.3 . . ?
N14 C13 C5 111.7(2) . . ?
N14 C13 C12 111.9(2) . . ?
N14 C13 H13 107.3 . . ?
C15 N14 C13 123.6(3) . . ?
C18 N14 C13 122.5(3) . . ?
C18 N14 C15 113.8(3) . . ?
N14 C15 H15A 110.9 . . ?
N14 C15 H15B 110.9 . . ?
N14 C15 C16 104.4(4) . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C15 C16 H16A 110.0 . . ?
C15 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 C15 108.4(4) . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
C16 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
C16 C17 C18 105.7(3) . . ?
H17A C17 H17B 108.7 . . ?
C18 C17 H17A 110.6 . . ?
C18 C17 H17B 110.6 . . ?
N14 C18 C17 107.3(4) . . ?
O20 C18 N14 125.3(3) . . ?
O20 C18 C17 127.4(4) . . ?
C1 O19 C21 118.4(3) . . ?
O19 C21 H21A 109.5 . . ?
O19 C21 H21B 109.5 . . ?
O19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C8 H8A O20 0.97 2.48 3.321(4) 145.0 4_454 yes
C9 H9B O20 0.97 2.46 3.335(4) 149.3 3_455 yes
C11 H11 O19 0.93 2.54 3.367(5) 148.9 1_455 yes

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 0.1(4) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C1 O19 C21 -3.8(5) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 N7 -178.7(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C13 177.8(2) . . . . ?
C3 C4 N7 C8 -161.4(3) . . . . ?
C3 C4 N7 C9 -20.4(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C13 C12 18.8(3) . . . . ?
C4 C5 C13 N14 144.5(2) . . . . ?
C4 N7 C8 C12 -50.8(3) . . . . ?
C4 N7 C9 C10 -66.6(4) . . . . ?
C5 C4 N7 C8 20.7(3) . . . . ?
C5 C4 N7 C9 161.7(2) . . . . ?
C5 C13 N14 C15 -69.5(3) . . . . ?
C5 C13 N14 C18 106.1(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C1 O19 C21 178.0(3) . . . . ?
C6 C5 C13 C12 -164.0(2) . . . . ?
C6 C5 C13 N14 -38.2(3) . . . . ?
N7 C4 C5 C6 178.6(2) . . . . ?
N7 C4 C5 C13 -4.2(3) . . . . ?
N7 C8 C12 C13 64.4(3) . . . . ?
C8 N7 C9 C10 75.5(4) . . . . ?
C8 C12 C13 C5 -47.5(3) . . . . ?
C8 C12 C13 N14 -173.1(2) . . . . ?
C9 N7 C8 C12 166.4(2) . . . . ?
C12 C13 N14 C15 55.9(4) . . . . ?
C12 C13 N14 C18 -128.5(3) . . . . ?
C13 C5 C6 C1 -177.0(2) . . . . ?
C13 N14 C15 C16 173.9(4) . . . . ?
C13 N14 C18 C17 -177.9(3) . . . . ?
C13 N14 C18 O20 2.4(4) . . . . ?
N14 C15 C16 C17 5.2(6) . . . . ?
C15 N14 C18 C17 -1.9(4) . . . . ?
C15 N14 C18 O20 178.4(3) . . . . ?
C15 C16 C17 C18 -6.4(6) . . . . ?
C16 C17 C18 N14 5.1(5) . . . . ?
C16 C17 C18 O20 -175.2(4) . . . . ?
C18 N14 C15 C16 -2.0(5) . . . . ?
O19 C1 C2 C3 -177.3(3) . . . . ?
O19 C1 C6 C5 177.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
