# 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_MZ_a
_database_code_depnum_ccdc_archive 'CCDC 2379026'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41

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                   15.1533(19)
_cell_length_b                   9.0554(11)
_cell_length_c                   15.2139(19)
_cell_angle_alpha                90
_cell_angle_beta                 115.586(3)
_cell_angle_gamma                90
_cell_volume                     1882.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25

_exptl_crystal_description       rod
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   0.921
_exptl_transmission_factor_max   0.987
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed_tube
_diffrn_measurement_device_type  Bruker_D8_VENTURE
_diffrn_measurement_method       omega_and_phi_scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68102
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.1384
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         25.159
_diffrn_reflns_theta_full        25.159
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3352
_reflns_number_gt                1807
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0374P)²+0.7429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
O1 O 0.57858(12) 0.3098(2) 0.47288(12) 0.0537(5) Uani 1 1 d . . . . .
N1 N 0.66660(19) 0.4508(3) 0.78810(16) 0.0690(7) Uani 1 1 d . . . . .
C7 C 0.51715(19) 0.2619(3) 0.5139(2) 0.0502(7) Uani 1 1 d . . . . .
C11 C 0.64616(19) 0.3786(3) 0.62881(18) 0.0497(7) Uani 1 1 d . . . . .
C20 C 0.72912(18) 0.4378(3) 0.51293(17) 0.0481(7) Uani 1 1 d . . . . .
C8 C 0.55651(19) 0.3038(3) 0.60821(19) 0.0516(7) Uani 1 1 d . . . . .
C13 C 0.7061(2) 0.4312(3) 0.72848(19) 0.0542(7) Uani 1 1 d . . . . .
C6 C 0.43008(19) 0.1831(3) 0.44966(19) 0.0496(7) Uani 1 1 d . . . . .
C10 C 0.65640(19) 0.3808(3) 0.54361(18) 0.0496(7) Uani 1 1 d . . . . .
C14 C 0.8129(2) 0.4546(3) 0.76812(18) 0.0547(7) Uani 1 1 d . . . . .
C1 C 0.3920(2) 0.1956(3) 0.3493(2) 0.0600(8) Uani 1 1 d . . . . .
C21 C 0.7720(2) 0.5745(4) 0.5439(2) 0.0591(8) Uani 1 1 d . . . . .
C19 C 0.8725(3) 0.3699(4) 0.7396(2) 0.0646(9) Uani 1 1 d . . . . .
C5 C 0.3801(2) 0.0921(3) 0.4872(2) 0.0611(8) Uani 1 1 d . . . . .
C9 C 0.5231(3) 0.2902(4) 0.6872(2) 0.0646(9) Uani 1 1 d . . . . .
C24 C 0.8299(2) 0.4033(4) 0.4289(2) 0.0710(10) Uani 1 1 d . . . . .
C23 C 0.8722(3) 0.5389(4) 0.4605(2) 0.0743(10) Uani 1 1 d . . . . .
C25 C 0.7581(2) 0.3529(4) 0.4541(2) 0.0601(8) Uani 1 1 d . . . . .
C4 C 0.2971(2) 0.0187(4) 0.4263(3) 0.0713(9) Uani 1 1 d . . . . .
C22 C 0.8430(2) 0.6251(4) 0.5174(2) 0.0707(9) Uani 1 1 d . . . . .
C12 C 0.5610(3) 0.4260(4) 0.7510(3) 0.0757(10) Uani 1 1 d . . . . .
C15 C 0.8578(3) 0.5623(4) 0.8394(2) 0.0741(9) Uani 1 1 d . . . . .
C2 C 0.3095(2) 0.1209(4) 0.2891(3) 0.0753(10) Uani 1 1 d . . . . .
C3 C 0.2610(3) 0.0329(4) 0.3275(3) 0.0752(10) Uani 1 1 d . . . . .
C18 C 0.9717(3) 0.3904(5) 0.7802(3) 0.0808(10) Uani 1 1 d . . . . .
C16 C 0.9566(3) 0.5832(5) 0.8788(3) 0.0906(11) Uani 1 1 d . . . . .
C17 C 1.0139(3) 0.4971(5) 0.8496(3) 0.0928(12) Uani 1 1 d . . . . .
H6A H 0.446(2) 0.287(3) 0.6572(17) 0.067(8) Uiso 1 1 d . . . . .
H6B H 0.5504(18) 0.199(3) 0.7260(19) 0.069(9) Uiso 1 1 d . . . . .
H5 H 0.4067(18) 0.082(3) 0.556(2) 0.060(8) Uiso 1 1 d . . . . .
H4 H 0.2667(19) -0.043(3) 0.4555(19) 0.074(9) Uiso 1 1 d . . . . .
H1 H 0.4261(18) 0.260(3) 0.3217(18) 0.067(8) Uiso 1 1 d . . . . .
H2 H 0.2844(19) 0.130(3) 0.219(2) 0.073(9) Uiso 1 1 d . . . . .
H3 H 0.203(2) -0.023(3) 0.285(2) 0.079(10) Uiso 1 1 d . . . . .
H7A H 0.522(2) 0.518(4) 0.711(2) 0.101(12) Uiso 1 1 d . . . . .
H7B H 0.547(2) 0.421(3) 0.806(2) 0.085(10) Uiso 1 1 d . . . . .
H12 H 0.8454(18) 0.301(3) 0.6954(19) 0.059(9) Uiso 1 1 d . . . . .
H11 H 1.011(3) 0.327(4) 0.759(2) 0.111(13) Uiso 1 1 d . . . . .
H9 H 0.991(3) 0.656(4) 0.931(3) 0.124(14) Uiso 1 1 d . . . . .
H8 H 0.816(2) 0.619(4) 0.861(2) 0.096(11) Uiso 1 1 d . . . . .
H10 H 1.084(2) 0.512(3) 0.880(2) 0.092(11) Uiso 1 1 d . . . . .
H17 H 0.7230(18) 0.260(3) 0.4295(18) 0.064(9) Uiso 1 1 d . . . . .
H14 H 0.873(2) 0.718(3) 0.5420(19) 0.073(10) Uiso 1 1 d . . . . .
H16 H 0.851(2) 0.341(4) 0.393(2) 0.098(12) Uiso 1 1 d . . . . .
H15 H 0.926(2) 0.576(4) 0.448(2) 0.104(11) Uiso 1 1 d . . . . .
H13 H 0.7519(17) 0.635(3) 0.5823(18) 0.059(8) Uiso 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 C10 1.366(3) . ?
O1 C7 1.395(3) . ?
N1 C13 1.296(3) . ?
N1 C12 1.466(4) . ?
C7 C8 1.349(3) . ?
C7 C6 1.446(4) . ?
C11 C10 1.371(3) . ?
C11 C8 1.427(3) . ?
C11 C13 1.470(4) . ?
C20 C21 1.383(4) . ?
C20 C25 1.388(4) . ?
C20 C10 1.464(3) . ?
C8 C9 1.497(4) . ?
C13 C14 1.479(4) . ?
C6 C1 1.384(4) . ?
C6 C5 1.397(4) . ?
C14 C19 1.389(4) . ?
C14 C15 1.397(4) . ?
C1 C2 1.367(4) . ?
C1 H1 0.99(3) . ?
C21 C22 1.380(4) . ?
C21 H13 0.94(2) . ?
C19 C18 1.369(5) . ?
C19 H12 0.88(3) . ?
C5 C4 1.371(4) . ?
C5 H5 0.95(3) . ?
C9 C12 1.518(4) . ?
C9 H6A 1.05(3) . ?
C9 H6B 0.99(3) . ?
C24 C23 1.372(5) . ?
C24 C25 1.377(4) . ?
C24 H16 0.94(3) . ?
C23 C22 1.373(5) . ?
C23 H15 0.97(3) . ?
C25 H17 0.98(3) . ?
C4 C3 1.365(4) . ?
C4 H4 0.95(3) . ?
C22 H14 0.96(3) . ?
C12 H7A 1.05(3) . ?
C12 H7B 0.95(3) . ?
C15 C16 1.364(5) . ?
C15 H8 0.97(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.97(3) . ?
C3 H3 0.98(3) . ?
C18 C17 1.369(5) . ?
C18 H11 0.98(4) . ?
C16 C17 1.375(5) . ?
C16 H9 0.99(4) . ?
C17 H10 0.96(3) . ?

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
C10 O1 C7 108.07(18) . . ?
C13 N1 C12 117.8(2) . . ?
C8 C7 O1 108.3(2) . . ?
C8 C7 C6 135.4(2) . . ?
O1 C7 C6 116.2(2) . . ?
C10 C11 C8 106.6(2) . . ?
C10 C11 C13 134.4(2) . . ?
C8 C11 C13 119.1(2) . . ?
C21 C20 C25 118.9(3) . . ?
C21 C20 C10 121.0(2) . . ?
C25 C20 C10 120.1(3) . . ?
C7 C8 C11 108.0(2) . . ?
C7 C8 C9 133.1(3) . . ?
C11 C8 C9 118.9(2) . . ?
N1 C13 C11 120.0(3) . . ?
N1 C13 C14 116.7(2) . . ?
C11 C13 C14 123.1(2) . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C7 122.0(2) . . ?
C5 C6 C7 120.8(2) . . ?
O1 C10 C11 109.1(2) . . ?
O1 C10 C20 115.3(2) . . ?
C11 C10 C20 135.6(3) . . ?
C19 C14 C15 117.6(3) . . ?
C19 C14 C13 122.6(3) . . ?
C15 C14 C13 119.8(3) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 H1 120.2(15) . . ?
C6 C1 H1 118.2(15) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H13 119.3(16) . . ?
C20 C21 H13 120.1(15) . . ?
C18 C19 C14 121.3(4) . . ?
C18 C19 H12 120.0(17) . . ?
C14 C19 H12 118.6(18) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 121.8(16) . . ?
C6 C5 H5 117.5(16) . . ?
C8 C9 C12 106.3(3) . . ?
C8 C9 H6A 110.4(14) . . ?
C12 C9 H6A 110.1(14) . . ?
C8 C9 H6B 110.4(15) . . ?
C12 C9 H6B 110.2(15) . . ?
H6A C9 H6B 109(2) . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H16 121(2) . . ?
C25 C24 H16 118(2) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H15 123(2) . . ?
C22 C23 H15 117(2) . . ?
C24 C25 C20 120.3(3) . . ?
C24 C25 H17 122.8(15) . . ?
C20 C25 H17 116.8(15) . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 121.8(16) . . ?
C5 C4 H4 117.3(16) . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H14 121.2(17) . . ?
C21 C22 H14 118.7(17) . . ?
N1 C12 C9 114.7(3) . . ?
N1 C12 H7A 110.2(18) . . ?
C9 C12 H7A 108.0(18) . . ?
N1 C12 H7B 107.3(18) . . ?
C9 C12 H7B 110.8(18) . . ?
H7A C12 H7B 105(2) . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H8 122(2) . . ?
C14 C15 H8 117(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 120.4(16) . . ?
C3 C2 H2 119.3(16) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 119.7(16) . . ?
C2 C3 H3 120.9(16) . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H11 118(2) . . ?
C17 C18 H11 122(2) . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H9 122(2) . . ?
C17 C16 H9 117(2) . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H10 121.3(19) . . ?
C16 C17 H10 118.7(19) . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
