# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mf5_a
_database_code_depnum_ccdc_archive 'CCDC 2264680'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N3 O2'
_chemical_formula_sum            'C13 H17 N3 O2'
_chemical_formula_weight         247.29

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6436(5)
_cell_length_b                   18.9145(12)
_cell_length_c                   8.3234(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.035(6)
_cell_angle_gamma                90
_cell_volume                     1343.90(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1920
_cell_measurement_theta_min      2.4280
_cell_measurement_theta_max      25.5680

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            8914
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3043
_reflns_number_gt                1847
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_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)+(0.0429P)²+0.3785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.2851(3) 0.46062(13) 0.4650(3) 0.0604(7) Uani 1 1 d . . . . .
H1A H 0.335730 0.466628 0.375276 0.072 Uiso 1 1 calc R U . . .
C2 C 0.2903(4) 0.51377(15) 0.5794(4) 0.0776(9) Uani 1 1 d . . . . .
H2A H 0.345890 0.554982 0.567038 0.093 Uiso 1 1 calc R U . . .
C3 C 0.2141(4) 0.50632(19) 0.7111(4) 0.0845(11) Uani 1 1 d . . . . .
H3A H 0.216286 0.542708 0.786514 0.101 Uiso 1 1 calc R U . . .
C4 C 0.1346(4) 0.4449(2) 0.7310(4) 0.0891(12) Uani 1 1 d . . . . .
H4A H 0.083911 0.439557 0.820835 0.107 Uiso 1 1 calc R U . . .
C5 C 0.1296(3) 0.39050(16) 0.6170(3) 0.0614(7) Uani 1 1 d . . . . .
H5A H 0.075724 0.348959 0.631012 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2050(2) 0.39847(12) 0.4828(3) 0.0396(5) Uani 1 1 d . . . . .
C7 C 0.1886(2) 0.34013(13) 0.3538(3) 0.0452(6) Uani 1 1 d . . . . .
H7A H 0.118742 0.304225 0.387969 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1135(3) 0.36566(15) 0.1896(3) 0.0621(8) Uani 1 1 d . . . . .
H8A H 0.018863 0.391626 0.200347 0.074 Uiso 1 1 calc R U . . .
H8B H 0.184371 0.397772 0.146640 0.074 Uiso 1 1 calc R U . . .
O9 O 0.07519(19) 0.30881(10) 0.0784(2) 0.0671(6) Uani 1 1 d . . . . .
H9A H -0.019997 0.307319 0.050064 0.081 Uiso 1 1 calc R U . . .
N10 N 0.33984(19) 0.30448(10) 0.3437(2) 0.0376(4) Uani 1 1 d . . . . .
N11 N 0.4528(2) 0.33699(10) 0.2773(2) 0.0438(5) Uani 1 1 d . . . . .
N12 N 0.57063(19) 0.29162(10) 0.2838(2) 0.0403(5) Uani 1 1 d . . . . .
C13 C 0.5326(2) 0.23038(11) 0.3543(2) 0.0343(5) Uani 1 1 d . . . . .
C14 C 0.3841(2) 0.23854(12) 0.3921(3) 0.0392(5) Uani 1 1 d . . . . .
H14A H 0.326577 0.205508 0.440674 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6434(2) 0.16727(12) 0.3810(3) 0.0411(5) Uani 1 1 d . . . . .
O16 O 0.75287(16) 0.17747(8) 0.52975(17) 0.0461(4) Uani 1 1 d . . . . .
H16A H 0.704812 0.188663 0.603341 0.055 Uiso 1 1 calc R U . . .
C17 C 0.5520(3) 0.09895(13) 0.3929(3) 0.0613(7) Uani 1 1 d . . . . .
H17A H 0.479382 0.092154 0.294323 0.092 Uiso 1 1 calc R U . . .
H17B H 0.623451 0.059806 0.408584 0.092 Uiso 1 1 calc R U . . .
H17C H 0.495594 0.101907 0.483263 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7443(3) 0.16302(15) 0.2461(3) 0.0650(8) Uani 1 1 d . . . . .
H18A H 0.678208 0.156210 0.143258 0.097 Uiso 1 1 calc R U . . .
H18B H 0.802363 0.206159 0.243361 0.097 Uiso 1 1 calc R U . . .
H18C H 0.815744 0.124029 0.266828 0.097 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 1.380(4) . ?
C1 C6 1.384(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.372(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.531(3) . ?
C7 N10 1.485(3) . ?
C7 C8 1.498(3) . ?
C7 H7A 0.9800 . ?
C8 O9 1.423(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O9 H9A 0.8200 . ?
N10 N11 1.344(2) . ?
N10 C14 1.347(3) . ?
N11 N12 1.326(2) . ?
N12 C13 1.362(3) . ?
C13 C14 1.377(3) . ?
C13 C15 1.525(3) . ?
C14 H14A 0.9300 . ?
C15 O16 1.449(2) . ?
C15 C17 1.526(3) . ?
C15 C18 1.528(3) . ?
O16 H16A 0.8200 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 120.5(3) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 122.0(2) . . ?
C5 C6 C7 118.9(2) . . ?
N10 C7 C8 110.73(19) . . ?
N10 C7 C6 112.44(17) . . ?
C8 C7 C6 112.8(2) . . ?
N10 C7 H7A 106.8 . . ?
C8 C7 H7A 106.8 . . ?
C6 C7 H7A 106.8 . . ?
O9 C8 C7 111.9(2) . . ?
O9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
O9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 O9 H9A 109.5 . . ?
N11 N10 C14 110.82(17) . . ?
N11 N10 C7 121.23(18) . . ?
C14 N10 C7 127.94(19) . . ?
N12 N11 N10 106.86(17) . . ?
N11 N12 C13 109.38(16) . . ?
N12 C13 C14 107.45(18) . . ?
N12 C13 C15 122.67(18) . . ?
C14 C13 C15 129.9(2) . . ?
N10 C14 C13 105.48(19) . . ?
N10 C14 H14A 127.3 . . ?
C13 C14 H14A 127.3 . . ?
O16 C15 C13 109.35(17) . . ?
O16 C15 C17 109.43(18) . . ?
C13 C15 C17 110.66(18) . . ?
O16 C15 C18 105.26(18) . . ?
C13 C15 C18 110.62(19) . . ?
C17 C15 C18 111.4(2) . . ?
C15 O16 H16A 109.5 . . ?
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 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C6 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C1 C6 C7 176.4(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -176.0(2) . . . . ?
C1 C6 C7 N10 68.9(3) . . . . ?
C5 C6 C7 N10 -114.9(2) . . . . ?
C1 C6 C7 C8 -57.1(3) . . . . ?
C5 C6 C7 C8 119.0(2) . . . . ?
N10 C7 C8 O9 62.9(3) . . . . ?
C6 C7 C8 O9 -170.11(19) . . . . ?
C8 C7 N10 N11 54.2(3) . . . . ?
C6 C7 N10 N11 -72.9(2) . . . . ?
C8 C7 N10 C14 -124.2(2) . . . . ?
C6 C7 N10 C14 108.6(2) . . . . ?
C14 N10 N11 N12 -0.3(2) . . . . ?
C7 N10 N11 N12 -178.99(18) . . . . ?
N10 N11 N12 C13 0.0(2) . . . . ?
N11 N12 C13 C14 0.3(2) . . . . ?
N11 N12 C13 C15 -179.67(18) . . . . ?
N11 N10 C14 C13 0.4(2) . . . . ?
C7 N10 C14 C13 179.04(19) . . . . ?
N12 C13 C14 N10 -0.4(2) . . . . ?
C15 C13 C14 N10 179.5(2) . . . . ?
N12 C13 C15 O16 83.2(2) . . . . ?
C14 C13 C15 O16 -96.7(3) . . . . ?
N12 C13 C15 C17 -156.2(2) . . . . ?
C14 C13 C15 C17 23.9(3) . . . . ?
N12 C13 C15 C18 -32.3(3) . . . . ?
C14 C13 C15 C18 147.8(2) . . . . ?

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
O9 H9A O16 0.82 1.97 2.764(2) 164.5 4_465 yes
C14 H14A O9 0.93 2.63 3.412(3) 142.7 4_566 yes
O16 H16A N12 0.82 2.07 2.888(2) 174.5 4_566 yes

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042

