# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_is_c8dd1
_database_code_depnum_ccdc_archive 'CCDC 2428779'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2025-03-04 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.5685(10)
_cell_length_b                   7.0647(4)
_cell_length_c                   16.3807(11)
_cell_angle_alpha                90
_cell_angle_beta                 116.123(2)
_cell_angle_gamma                90
_cell_volume                     1513.72(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      32.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'

#==============================================================================

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            65236
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         30.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4820
_reflns_number_gt                4157
_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 Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²+0.4982P] 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         4820
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.38058(5) 0.82191(12) 0.37147(5) 0.02320(17) Uani 1 1 d . . . . .
O2 O 0.72736(5) 0.79714(11) 0.50488(5) 0.02158(16) Uani 1 1 d . . . . .
N1 N 0.55355(6) 0.81160(11) 0.43780(5) 0.01510(15) Uani 1 1 d . . . . .
N2 N 0.64622(6) 0.69694(11) 0.58839(5) 0.01457(15) Uani 1 1 d . . . . .
N3 N 0.55688(6) 0.64007(11) 0.68001(5) 0.01390(15) Uani 1 1 d . . . . .
C1 C 0.55650(6) 0.68722(12) 0.59761(6) 0.01334(16) Uani 1 1 d . . . . .
C2 C 0.46355(6) 0.72651(13) 0.52530(6) 0.01412(16) Uani 1 1 d . . . . .
C3 C 0.46030(7) 0.78745(13) 0.43972(6) 0.01520(17) Uani 1 1 d . . . . .
C4 C 0.64743(7) 0.77240(13) 0.51003(6) 0.01565(17) Uani 1 1 d . . . . .
C5 C 0.55161(7) 0.87507(14) 0.35176(6) 0.01854(18) Uani 1 1 d . . . . .
H5A H 0.6207 0.9115 0.3619 0.028 Uiso 1 1 calc R U . . .
H5B H 0.5058 0.9841 0.3286 0.028 Uiso 1 1 calc R U . . .
H5C H 0.5270 0.7719 0.3073 0.028 Uiso 1 1 calc R U . . .
C6 C 0.74270(7) 0.60247(15) 0.64940(7) 0.01994(19) Uani 1 1 d . . . . .
H6A H 0.7805 0.5670 0.6148 0.030 Uiso 1 1 calc R U . . .
H6B H 0.7274 0.4886 0.6753 0.030 Uiso 1 1 calc R U . . .
H6C H 0.7843 0.6891 0.6985 0.030 Uiso 1 1 calc R U . . .
C7 C 0.63709(7) 0.61719(14) 0.76634(6) 0.01814(18) Uani 1 1 d . . . . .
H7 H 0.7078 0.6274 0.7815 0.022 Uiso 1 1 calc R U . . .
C8 C 0.59657(7) 0.57749(15) 0.82558(6) 0.02022(19) Uani 1 1 d . . . . .
H8 H 0.6347 0.5537 0.8888 0.024 Uiso 1 1 calc R U . . .
C9 C 0.48890(7) 0.57765(14) 0.77740(6) 0.01800(18) Uani 1 1 d . . . . .
H9 H 0.4423 0.5539 0.8024 0.022 Uiso 1 1 calc R U . . .
C10 C 0.46337(7) 0.61837(13) 0.68755(6) 0.01439(17) Uani 1 1 d . . . . .
C11 C 0.36775(7) 0.65432(13) 0.61095(6) 0.01459(17) Uani 1 1 d . . . . .
C12 C 0.36958(7) 0.71124(13) 0.53220(6) 0.01528(17) Uani 1 1 d . . . . .
H12 H 0.3072 0.7413 0.4810 0.018 Uiso 1 1 calc R U . . .
C13 C 0.27008(7) 0.64062(13) 0.61808(6) 0.01591(17) Uani 1 1 d . . . . .
C14 C 0.24661(7) 0.48672(14) 0.65901(7) 0.02091(19) Uani 1 1 d . . . . .
H14 H 0.2963 0.3908 0.6873 0.025 Uiso 1 1 calc R U . . .
C15 C 0.15111(8) 0.47259(15) 0.65866(7) 0.0222(2) Uani 1 1 d . . . . .
H15 H 0.1369 0.3674 0.6874 0.027 Uiso 1 1 calc R U . . .
C16 C 0.07596(7) 0.60928(15) 0.61714(7) 0.01898(19) Uani 1 1 d . . . . .
C17 C 0.10090(7) 0.76582(15) 0.57899(7) 0.01925(19) Uani 1 1 d . . . . .
H17 H 0.0516 0.8630 0.5520 0.023 Uiso 1 1 calc R U . . .
C18 C 0.19625(7) 0.78268(14) 0.57964(6) 0.01760(18) Uani 1 1 d . . . . .
H18 H 0.2115 0.8915 0.5538 0.021 Uiso 1 1 calc R U . . .
C19 C -0.02956(7) 0.58791(16) 0.61152(7) 0.0232(2) Uani 1 1 d . . . . .
H19A H -0.0476 0.7030 0.6346 0.035 Uiso 1 1 calc R U . . .
H19B H -0.0307 0.4792 0.6482 0.035 Uiso 1 1 calc R U . . .
H19C H -0.0790 0.5677 0.5481 0.035 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C3 1.2307(11) . ?
O2 C4 1.2165(11) . ?
N1 C3 1.3832(11) . ?
N1 C4 1.3864(12) . ?
N1 C5 1.4673(12) . ?
N2 C1 1.3821(11) . ?
N2 C4 1.3970(12) . ?
N2 C6 1.4775(12) . ?
N3 C1 1.3878(11) . ?
N3 C7 1.3915(11) . ?
N3 C10 1.4292(11) . ?
C1 C2 1.3788(12) . ?
C2 C12 1.4265(12) . ?
C2 C3 1.4473(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3687(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4117(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.3803(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.4284(12) . ?
C11 C12 1.3627(13) . ?
C11 C13 1.4811(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.3966(13) . ?
C13 C18 1.4015(13) . ?
C14 C15 1.3924(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.3922(14) . ?
C15 H15 0.9500 . ?
C16 C17 1.3949(14) . ?
C16 C19 1.5066(13) . ?
C17 C18 1.3895(12) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C3 N1 C4 124.45(8) . . ?
C3 N1 C5 117.11(7) . . ?
C4 N1 C5 118.38(7) . . ?
C1 N2 C4 120.97(7) . . ?
C1 N2 C6 124.57(8) . . ?
C4 N2 C6 113.62(7) . . ?
C1 N3 C7 131.17(8) . . ?
C1 N3 C10 120.93(7) . . ?
C7 N3 C10 107.79(7) . . ?
C2 C1 N2 120.96(8) . . ?
C2 C1 N3 117.75(8) . . ?
N2 C1 N3 121.28(8) . . ?
C1 C2 C12 122.04(8) . . ?
C1 C2 C3 119.53(8) . . ?
C12 C2 C3 118.43(8) . . ?
O1 C3 N1 119.90(8) . . ?
O1 C3 C2 123.64(8) . . ?
N1 C3 C2 116.43(8) . . ?
O2 C4 N1 121.79(9) . . ?
O2 C4 N2 121.21(8) . . ?
N1 C4 N2 116.97(8) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N3 108.24(8) . . ?
C8 C7 H7 125.9 . . ?
N3 C7 H7 125.9 . . ?
C7 C8 C9 108.86(8) . . ?
C7 C8 H8 125.6 . . ?
C9 C8 H8 125.6 . . ?
C10 C9 C8 107.93(8) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
C9 C10 C11 132.40(8) . . ?
C9 C10 N3 107.15(8) . . ?
C11 C10 N3 120.21(8) . . ?
C12 C11 C10 117.77(8) . . ?
C12 C11 C13 120.92(8) . . ?
C10 C11 C13 121.23(8) . . ?
C11 C12 C2 121.12(8) . . ?
C11 C12 H12 119.4 . . ?
C2 C12 H12 119.4 . . ?
C14 C13 C18 118.13(8) . . ?
C14 C13 C11 122.37(8) . . ?
C18 C13 C11 119.45(8) . . ?
C15 C14 C13 120.61(9) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 121.45(9) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 117.70(9) . . ?
C15 C16 C19 121.48(9) . . ?
C17 C16 C19 120.81(9) . . ?
C18 C17 C16 121.42(9) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 120.60(9) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C4 N2 C1 C2 9.20(13) . . . . ?
C6 N2 C1 C2 -159.66(9) . . . . ?
C4 N2 C1 N3 -169.97(8) . . . . ?
C6 N2 C1 N3 21.17(13) . . . . ?
C7 N3 C1 C2 -170.74(9) . . . . ?
C10 N3 C1 C2 4.87(13) . . . . ?
C7 N3 C1 N2 8.47(15) . . . . ?
C10 N3 C1 N2 -175.93(8) . . . . ?
N2 C1 C2 C12 177.82(8) . . . . ?
N3 C1 C2 C12 -2.97(13) . . . . ?
N2 C1 C2 C3 -2.94(13) . . . . ?
N3 C1 C2 C3 176.27(8) . . . . ?
C4 N1 C3 O1 -178.31(9) . . . . ?
C5 N1 C3 O1 -1.15(13) . . . . ?
C4 N1 C3 C2 3.39(13) . . . . ?
C5 N1 C3 C2 -179.44(8) . . . . ?
C1 C2 C3 O1 178.61(9) . . . . ?
C12 C2 C3 O1 -2.13(14) . . . . ?
C1 C2 C3 N1 -3.16(13) . . . . ?
C12 C2 C3 N1 176.10(8) . . . . ?
C3 N1 C4 O2 -179.62(9) . . . . ?
C5 N1 C4 O2 3.25(14) . . . . ?
C3 N1 C4 N2 2.45(13) . . . . ?
C5 N1 C4 N2 -174.68(8) . . . . ?
C1 N2 C4 O2 173.26(9) . . . . ?
C6 N2 C4 O2 -16.74(13) . . . . ?
C1 N2 C4 N1 -8.80(13) . . . . ?
C6 N2 C4 N1 161.20(8) . . . . ?
C1 N3 C7 C8 177.65(9) . . . . ?
C10 N3 C7 C8 1.61(11) . . . . ?
N3 C7 C8 C9 -0.94(12) . . . . ?
C7 C8 C9 C10 -0.12(12) . . . . ?
C8 C9 C10 C11 -173.14(10) . . . . ?
C8 C9 C10 N3 1.09(11) . . . . ?
C1 N3 C10 C9 -178.20(8) . . . . ?
C7 N3 C10 C9 -1.67(10) . . . . ?
C1 N3 C10 C11 -3.12(13) . . . . ?
C7 N3 C10 C11 173.40(8) . . . . ?
C9 C10 C11 C12 172.89(10) . . . . ?
N3 C10 C11 C12 -0.74(13) . . . . ?
C9 C10 C11 C13 -3.79(16) . . . . ?
N3 C10 C11 C13 -177.41(8) . . . . ?
C10 C11 C12 C2 2.66(13) . . . . ?
C13 C11 C12 C2 179.35(8) . . . . ?
C1 C2 C12 C11 -0.86(14) . . . . ?
C3 C2 C12 C11 179.90(9) . . . . ?
C12 C11 C13 C14 135.87(10) . . . . ?
C10 C11 C13 C14 -47.56(13) . . . . ?
C12 C11 C13 C18 -41.65(13) . . . . ?
C10 C11 C13 C18 134.92(9) . . . . ?
C18 C13 C14 C15 2.13(15) . . . . ?
C11 C13 C14 C15 -175.42(9) . . . . ?
C13 C14 C15 C16 0.59(16) . . . . ?
C14 C15 C16 C17 -2.64(15) . . . . ?
C14 C15 C16 C19 176.05(9) . . . . ?
C15 C16 C17 C18 1.99(15) . . . . ?
C19 C16 C17 C18 -176.72(9) . . . . ?
C16 C17 C18 C13 0.72(15) . . . . ?
C14 C13 C18 C17 -2.77(14) . . . . ?
C11 C13 C18 C17 174.85(8) . . . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.058



