# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_SNDMS23
_database_code_depnum_ccdc_archive 'CCDC 2419876'
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O0'
_chemical_formula_iupac          ?
_chemical_formula_weight         286.36

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9539(3)
_cell_length_b                   11.1308(6)
_cell_length_c                   11.7050(7)
_cell_angle_alpha                78.746(2)
_cell_angle_beta                 86.935(2)
_cell_angle_gamma                79.975(2)
_cell_volume                     749.03(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5716
_cell_measurement_theta_min      2.3367
_cell_measurement_theta_max      30.2946
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       PLATES
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.051
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_T_max  0.9960

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            27469
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             4565
_reflns_number_gt                3168
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1360
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         4565
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.3242P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.38499(19) 0.68216(11) 0.52109(10) 0.0213(2) Uani d . . . 1 . .
N N2 0.58569(19) 0.82476(11) 0.64204(10) 0.0222(2) Uani d . . . 1 . .
C C1 0.6438(2) 0.82008(12) 0.53102(12) 0.0207(3) Uani d . . . 1 . .
C C2 0.8253(2) 0.89260(14) 0.47718(13) 0.0246(3) Uani d . . . 1 . .
H H2A 0.95625 0.873532 0.530182 0.03 Uiso calc U . R 1 . .
H H2B 0.764394 0.982439 0.468605 0.03 Uiso calc U . R 1 . .
C C3 0.9090(3) 0.86424(15) 0.35837(13) 0.0272(3) Uani d . . . 1 . .
H H3A 0.996796 0.928539 0.318094 0.033 Uiso calc U . R 1 . .
H H3B 1.011283 0.782818 0.368634 0.033 Uiso calc U . R 1 . .
C C4 0.7074(3) 0.86161(15) 0.28472(13) 0.0300(3) Uani d . . . 1 . .
H H4A 0.762056 0.850651 0.205438 0.036 Uiso calc U . R 1 . .
H H4B 0.600898 0.941494 0.277843 0.036 Uiso calc U . R 1 . .
C C5 0.5833(3) 0.75522(14) 0.34062(12) 0.0258(3) Uani d . . . 1 . .
H H5A 0.438008 0.763548 0.30013 0.031 Uiso calc U . R 1 . .
H H5B 0.677983 0.675391 0.330667 0.031 Uiso calc U . R 1 . .
C C6 0.5337(2) 0.75314(12) 0.46823(12) 0.0205(3) Uani d . . . 1 . .
C C7 0.3337(2) 0.68146(12) 0.63442(11) 0.0201(3) Uani d . . . 1 . .
C C8 0.4266(2) 0.75929(13) 0.69341(12) 0.0212(3) Uani d . . . 1 . .
C C9 0.1772(2) 0.59538(12) 0.68937(12) 0.0212(3) Uani d . . . 1 . .
C C10 0.0094(2) 0.57176(13) 0.62164(13) 0.0231(3) Uani d . . . 1 . .
H H10 -0.000403 0.609629 0.541576 0.028 Uiso calc U . R 1 . .
C C11 -0.1431(2) 0.49379(14) 0.66974(14) 0.0270(3) Uani d . . . 1 . .
H H11 -0.258165 0.479667 0.623142 0.032 Uiso calc U . R 1 . .
C C12 -0.1272(3) 0.43666(14) 0.78575(14) 0.0315(3) Uani d . . . 1 . .
H H12 -0.233032 0.384355 0.819331 0.038 Uiso calc U . R 1 . .
C C13 0.0434(3) 0.45578(14) 0.85299(13) 0.0314(3) Uani d . . . 1 . .
H H13 0.056539 0.414693 0.93209 0.038 Uiso calc U . R 1 . .
C C14 0.1948(3) 0.53452(13) 0.80547(12) 0.0268(3) Uani d . . . 1 . .
H H14 0.311114 0.547127 0.852173 0.032 Uiso calc U . R 1 . .
C C15 0.3531(2) 0.78190(13) 0.81178(12) 0.0229(3) Uani d . . . 1 . .
C C16 0.1258(3) 0.82423(13) 0.83692(13) 0.0255(3) Uani d . . . 1 . .
H H16 0.01331 0.832299 0.780078 0.031 Uiso calc U . R 1 . .
C C17 0.0627(3) 0.85474(14) 0.94488(14) 0.0307(3) Uani d . . . 1 . .
H H17 -0.092658 0.884604 0.961489 0.037 Uiso calc U . R 1 . .
C C18 0.2252(3) 0.84177(15) 1.02819(14) 0.0340(4) Uani d . . . 1 . .
H H18 0.181698 0.863541 1.101726 0.041 Uiso calc U . R 1 . .
C C19 0.4508(3) 0.79726(17) 1.00498(14) 0.0367(4) Uani d . . . 1 . .
H H19 0.5618 0.786484 1.063103 0.044 Uiso calc U . R 1 . .
C C20 0.5152(3) 0.76829(16) 0.89655(13) 0.0307(3) Uani d . . . 1 . .
H H20 0.670921 0.738997 0.880195 0.037 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 . 1.3359(17) ?
N1 C7 . 1.3441(17) ?
N2 C1 . 1.3354(17) ?
N2 C8 . 1.3408(18) ?
C1 C6 . 1.4003(19) ?
C1 C2 . 1.4997(19) ?
C2 C3 . 1.524(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.522(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.525(2) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.5035(19) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C7 C8 . 1.4053(19) ?
C7 C9 . 1.4850(19) ?
C8 C15 . 1.4857(18) ?
C9 C14 . 1.3956(19) ?
C9 C10 . 1.3979(19) ?
C10 C11 . 1.387(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.383(2) ?
C11 H11 . 0.95 ?
C12 C13 . 1.386(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.386(2) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C16 . 1.389(2) ?
C15 C20 . 1.390(2) ?
C16 C17 . 1.388(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.381(2) ?
C17 H17 . 0.95 ?
C18 C19 . 1.380(2) ?
C18 H18 . 0.95 ?
C19 C20 . 1.388(2) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C7 . . 118.70(12) ?
C1 N2 C8 . . 118.37(12) ?
N2 C1 C6 . . 120.76(12) ?
N2 C1 C2 . . 116.85(12) ?
C6 C1 C2 . . 122.36(12) ?
C1 C2 C3 . . 112.99(12) ?
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 ?
C4 C3 C2 . . 110.20(12) ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3B . . 109.6 ?
C2 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C3 C4 C5 . . 110.05(12) ?
C3 C4 H4A . . 109.7 ?
C5 C4 H4A . . 109.7 ?
C3 C4 H4B . . 109.7 ?
C5 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
C6 C5 C4 . . 112.28(12) ?
C6 C5 H5A . . 109.1 ?
C4 C5 H5A . . 109.1 ?
C6 C5 H5B . . 109.1 ?
C4 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C1 . . 120.73(12) ?
N1 C6 C5 . . 117.73(12) ?
C1 C6 C5 . . 121.51(12) ?
N1 C7 C8 . . 119.99(12) ?
N1 C7 C9 . . 115.90(12) ?
C8 C7 C9 . . 124.10(12) ?
N2 C8 C7 . . 120.88(12) ?
N2 C8 C15 . . 114.51(12) ?
C7 C8 C15 . . 124.53(12) ?
C14 C9 C10 . . 118.55(13) ?
C14 C9 C7 . . 122.55(13) ?
C10 C9 C7 . . 118.88(12) ?
C11 C10 C9 . . 120.90(14) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C12 C11 C10 . . 119.81(14) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 119.94(14) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C14 C13 C12 . . 120.38(14) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C9 . . 120.35(14) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
C16 C15 C20 . . 119.30(13) ?
C16 C15 C8 . . 120.83(13) ?
C20 C15 C8 . . 119.74(13) ?
C17 C16 C15 . . 120.14(14) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C18 C17 C16 . . 120.11(15) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C19 C18 C17 . . 120.21(15) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C20 . . 119.87(15) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C19 C20 C15 . . 120.36(15) ?
C19 C20 H20 . . 119.8 ?
C15 C20 H20 . . 119.8 ?

