# 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_lk5950_lt_0ma
_database_code_depnum_ccdc_archive 'CCDC 2402787'
loop_
_audit_author_name
_audit_author_address
'Anton P. Novikov'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-11-14 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-09-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O'
_chemical_formula_sum            'C19 H16 N2 O'
_chemical_formula_weight         288.34
_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           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                   15.7758(14)
_cell_length_b                   5.9637(6)
_cell_length_c                   15.5467(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.558(4)
_cell_angle_gamma                90
_cell_volume                     1461.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.387
_cell_measurement_theta_min      2.584
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0688 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.9218.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20681
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         4.286
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_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                2133
_reflns_number_total             3347
_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 (Bruker, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0067(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.029
_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)+(0.0364P)²+0.3927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.14742(8) -0.02418(19) 0.31517(8) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.18525(9) 0.2966(2) 0.39217(9) 0.0190(4) Uani 1 1 d . . . . .
N1 N 0.29746(10) 0.0427(3) 0.21228(9) 0.0202(4) Uani 1 1 d . . . . .
H1 H 0.2688(13) -0.081(3) 0.1919(12) 0.034(6) Uiso 1 1 d . . . . .
C13 C 0.15300(12) 0.5582(3) 0.53369(12) 0.0214(4) Uani 1 1 d . . . . .
H13 H 0.1226(12) 0.414(3) 0.5214(11) 0.024(5) Uiso 1 1 d . . . . .
C18 C 0.07472(12) -0.0388(3) 0.36887(12) 0.0205(4) Uani 1 1 d . . . . .
H18A H 0.0958(11) -0.052(3) 0.4313(11) 0.017(5) Uiso 1 1 d . . . . .
H18B H 0.0402(12) 0.106(3) 0.3625(11) 0.022(5) Uiso 1 1 d . . . . .
C8 C 0.23899(11) 0.4747(3) 0.40659(11) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.41153(12) 0.0880(3) 0.10605(12) 0.0210(4) Uani 1 1 d . . . . .
H4 H 0.3977(12) -0.059(3) 0.0746(12) 0.031(5) Uiso 1 1 d . . . . .
C9 C 0.30751(12) 0.5138(3) 0.35628(11) 0.0178(4) Uani 1 1 d . . . . .
H9 H 0.3458(12) 0.644(3) 0.3642(11) 0.022(5) Uiso 1 1 d . . . . .
C3 C 0.47467(12) 0.2328(3) 0.08192(12) 0.0234(4) Uani 1 1 d . . . . .
H3 H 0.5077(12) 0.196(3) 0.0310(12) 0.028(5) Uiso 1 1 d . . . . .
C2 C 0.49348(13) 0.4327(3) 0.12744(12) 0.0232(4) Uani 1 1 d . . . . .
H2 H 0.5407(13) 0.530(3) 0.1066(12) 0.028(5) Uiso 1 1 d . . . . .
C6 C 0.27008(11) 0.1735(3) 0.27930(11) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.26009(12) 0.8226(3) 0.49766(12) 0.0208(4) Uani 1 1 d . . . . .
H17 H 0.3065(12) 0.876(3) 0.4616(11) 0.025(5) Uiso 1 1 d . . . . .
C14 C 0.13206(13) 0.6919(3) 0.60264(12) 0.0241(5) Uani 1 1 d . . . . .
H14 H 0.0871(13) 0.643(3) 0.6416(12) 0.031(5) Uiso 1 1 d . . . . .
C19 C 0.02492(14) -0.2431(3) 0.33974(14) 0.0258(5) Uani 1 1 d . . . . .
H19A H -0.0273(14) -0.261(3) 0.3757(13) 0.038(6) Uiso 1 1 d . . . . .
H19B H 0.0043(13) -0.227(3) 0.2774(13) 0.034(6) Uiso 1 1 d . . . . .
H19C H 0.0610(14) -0.382(4) 0.3443(13) 0.044(6) Uiso 1 1 d . . . . .
C16 C 0.23872(13) 0.9567(3) 0.56614(12) 0.0243(5) Uani 1 1 d . . . . .
H16 H 0.2695(12) 1.098(3) 0.5756(11) 0.024(5) Uiso 1 1 d . . . . .
C15 C 0.17456(13) 0.8919(3) 0.61948(12) 0.0257(5) Uani 1 1 d . . . . .
H15 H 0.1592(12) 0.994(3) 0.6676(12) 0.027(5) Uiso 1 1 d . . . . .
C7 C 0.20044(11) 0.1520(3) 0.33104(11) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.38412(11) 0.3473(3) 0.22392(11) 0.0176(4) Uani 1 1 d . . . . .
C5 C 0.36598(11) 0.1477(3) 0.17735(11) 0.0181(4) Uani 1 1 d . . . . .
C1 C 0.44856(12) 0.4902(3) 0.19837(12) 0.0197(4) Uani 1 1 d . . . . .
H1A H 0.4586(12) 0.635(3) 0.2301(11) 0.027(5) Uiso 1 1 d . . . . .
C12 C 0.21781(11) 0.6206(3) 0.48000(11) 0.0178(4) Uani 1 1 d . . . . .
C10 C 0.32309(11) 0.3602(3) 0.29011(11) 0.0170(4) Uani 1 1 d . . . . .


_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 C18 1.451(2) . ?
O1 C7 1.359(2) . ?
N2 C8 1.371(2) . ?
N2 C7 1.313(2) . ?
N1 H1 0.92(2) . ?
N1 C6 1.386(2) . ?
N1 C5 1.381(2) . ?
C13 H13 0.997(19) . ?
C13 C14 1.388(2) . ?
C13 C12 1.399(3) . ?
C18 H18A 1.015(17) . ?
C18 H18B 1.024(18) . ?
C18 C19 1.508(3) . ?
C8 C9 1.382(2) . ?
C8 C12 1.485(2) . ?
C4 H4 1.020(19) . ?
C4 C3 1.383(3) . ?
C4 C5 1.394(2) . ?
C9 H9 0.988(18) . ?
C9 C10 1.407(2) . ?
C3 H3 0.992(18) . ?
C3 C2 1.411(3) . ?
C2 H2 1.009(19) . ?
C2 C1 1.380(3) . ?
C6 C7 1.396(2) . ?
C6 C10 1.398(2) . ?
C17 H17 0.994(18) . ?
C17 C16 1.385(2) . ?
C17 C12 1.398(2) . ?
C14 H14 1.00(2) . ?
C14 C15 1.388(3) . ?
C19 H19A 1.02(2) . ?
C19 H19B 1.01(2) . ?
C19 H19C 1.01(2) . ?
C16 H16 0.980(19) . ?
C16 C15 1.391(3) . ?
C15 H15 1.002(18) . ?
C11 C5 1.416(2) . ?
C11 C1 1.398(2) . ?
C11 C10 1.442(2) . ?
C1 H1A 1.001(18) . ?

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
C7 O1 C18 115.96(13) . . ?
C7 N2 C8 119.71(15) . . ?
C6 N1 H1 123.3(12) . . ?
C5 N1 H1 127.8(12) . . ?
C5 N1 C6 108.42(15) . . ?
C14 C13 H13 120.8(10) . . ?
C14 C13 C12 120.91(18) . . ?
C12 C13 H13 118.2(10) . . ?
O1 C18 H18A 108.8(10) . . ?
O1 C18 H18B 108.9(10) . . ?
O1 C18 C19 106.86(15) . . ?
H18A C18 H18B 107.8(13) . . ?
C19 C18 H18A 111.8(10) . . ?
C19 C18 H18B 112.7(10) . . ?
N2 C8 C9 122.13(16) . . ?
N2 C8 C12 114.89(15) . . ?
C9 C8 C12 122.98(16) . . ?
C3 C4 H4 123.1(11) . . ?
C3 C4 C5 117.35(17) . . ?
C5 C4 H4 119.6(11) . . ?
C8 C9 H9 123.4(10) . . ?
C8 C9 C10 118.05(16) . . ?
C10 C9 H9 118.5(10) . . ?
C4 C3 H3 119.3(11) . . ?
C4 C3 C2 121.97(18) . . ?
C2 C3 H3 118.7(11) . . ?
C3 C2 H2 117.8(10) . . ?
C1 C2 C3 120.43(18) . . ?
C1 C2 H2 121.7(10) . . ?
N1 C6 C7 131.37(16) . . ?
N1 C6 C10 109.50(15) . . ?
C7 C6 C10 119.07(15) . . ?
C16 C17 H17 117.3(11) . . ?
C16 C17 C12 121.19(18) . . ?
C12 C17 H17 121.5(11) . . ?
C13 C14 H14 120.1(11) . . ?
C13 C14 C15 120.66(19) . . ?
C15 C14 H14 119.2(11) . . ?
C18 C19 H19A 109.9(11) . . ?
C18 C19 H19B 110.5(11) . . ?
C18 C19 H19C 111.0(12) . . ?
H19A C19 H19B 107.5(15) . . ?
H19A C19 H19C 110.2(16) . . ?
H19B C19 H19C 107.7(16) . . ?
C17 C16 H16 118.3(11) . . ?
C17 C16 C15 120.41(18) . . ?
C15 C16 H16 121.2(11) . . ?
C14 C15 C16 118.97(18) . . ?
C14 C15 H15 122.0(11) . . ?
C16 C15 H15 119.0(11) . . ?
O1 C7 C6 117.41(15) . . ?
N2 C7 O1 120.58(16) . . ?
N2 C7 C6 122.01(16) . . ?
C5 C11 C10 106.47(15) . . ?
C1 C11 C5 120.02(16) . . ?
C1 C11 C10 133.42(16) . . ?
N1 C5 C4 129.58(16) . . ?
N1 C5 C11 108.91(15) . . ?
C4 C5 C11 121.45(16) . . ?
C2 C1 C11 118.78(17) . . ?
C2 C1 H1A 122.1(11) . . ?
C11 C1 H1A 119.0(11) . . ?
C13 C12 C8 119.88(16) . . ?
C17 C12 C13 117.84(16) . . ?
C17 C12 C8 122.28(16) . . ?
C9 C10 C11 134.45(17) . . ?
C6 C10 C9 118.89(16) . . ?
C6 C10 C11 106.65(15) . . ?

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
N2 C8 C9 C10 -2.0(3) . . . . ?
N2 C8 C12 C13 6.7(2) . . . . ?
N2 C8 C12 C17 -172.70(16) . . . . ?
N1 C6 C7 O1 -0.8(3) . . . . ?
N1 C6 C7 N2 -179.90(17) . . . . ?
N1 C6 C10 C9 -178.77(15) . . . . ?
N1 C6 C10 C11 2.35(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C18 O1 C7 N2 0.4(2) . . . . ?
C18 O1 C7 C6 -178.71(16) . . . . ?
C8 N2 C7 O1 -179.30(15) . . . . ?
C8 N2 C7 C6 -0.2(2) . . . . ?
C8 C9 C10 C6 -1.3(2) . . . . ?
C8 C9 C10 C11 177.21(18) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C9 C8 C12 C13 -173.31(17) . . . . ?
C9 C8 C12 C17 7.3(3) . . . . ?
C3 C4 C5 N1 176.02(18) . . . . ?
C3 C4 C5 C11 -0.7(3) . . . . ?
C3 C2 C1 C11 -0.2(3) . . . . ?
C6 N1 C5 C4 -175.77(18) . . . . ?
C6 N1 C5 C11 1.3(2) . . . . ?
C17 C16 C15 C14 -0.4(3) . . . . ?
C14 C13 C12 C8 -179.98(16) . . . . ?
C14 C13 C12 C17 -0.6(3) . . . . ?
C16 C17 C12 C13 0.1(3) . . . . ?
C16 C17 C12 C8 179.50(16) . . . . ?
C7 O1 C18 C19 179.48(15) . . . . ?
C7 N2 C8 C9 2.8(2) . . . . ?
C7 N2 C8 C12 -177.16(15) . . . . ?
C7 C6 C10 C9 3.7(2) . . . . ?
C7 C6 C10 C11 -175.16(15) . . . . ?
C5 N1 C6 C7 174.82(18) . . . . ?
C5 N1 C6 C10 -2.3(2) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
C5 C11 C1 C2 0.0(3) . . . . ?
C5 C11 C10 C9 179.84(19) . . . . ?
C5 C11 C10 C6 -1.54(19) . . . . ?
C1 C11 C5 N1 -176.90(16) . . . . ?
C1 C11 C5 C4 0.4(3) . . . . ?
C1 C11 C10 C9 -3.6(4) . . . . ?
C1 C11 C10 C6 175.00(19) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C12 C8 C9 C10 177.98(15) . . . . ?
C12 C17 C16 C15 0.4(3) . . . . ?
C10 C6 C7 O1 176.06(15) . . . . ?
C10 C6 C7 N2 -3.0(3) . . . . ?
C10 C11 C5 N1 0.19(19) . . . . ?
C10 C11 C5 C4 177.51(16) . . . . ?
C10 C11 C1 C2 -176.12(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT910_lk5950_lt_0ma       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
