# Electronic Supplementary Material (ESI) 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_Mp
_database_code_depnum_ccdc_archive 'CCDC 2315214'
loop_
_audit_author_name
_audit_author_address
'Youpeng Zuo'
;SUZHOU UNIVERSITY
China
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35

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'

_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                   8.0992(4)
_cell_length_b                   20.6903(11)
_cell_length_c                   9.9276(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.728(2)
_cell_angle_gamma                90
_cell_volume                     1545.42(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9659
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61845
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.958
_diffrn_reflns_theta_max         27.625
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3540
_reflns_number_gt                3175
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0458P)²+0.6533P] 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         3540
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.0949(2) 0.15222(7) 0.35325(16) 0.0431(3) Uani 1 1 d . . . . .
H1 H 0.009008 0.153495 0.259990 0.052 Uiso 1 1 calc R U . . .
C2 C 0.0908(2) 0.19705(9) 0.4560(2) 0.0556(4) Uani 1 1 d . . . . .
H2 H 0.000566 0.227728 0.431995 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2200(3) 0.19625(9) 0.59351(19) 0.0579(4) Uani 1 1 d . . . . .
H3 H 0.217494 0.226542 0.661922 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3525(2) 0.15062(8) 0.62921(16) 0.0528(4) Uani 1 1 d . . . . .
H4 H 0.440811 0.150749 0.721411 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3558(2) 0.10441(7) 0.52924(15) 0.0410(3) Uani 1 1 d . . . . .
H5 H 0.443538 0.072762 0.555228 0.049 Uiso 1 1 calc R U . . .
C6 C 0.22690(17) 0.10559(6) 0.38960(14) 0.0338(3) Uani 1 1 d . . . . .
C7 C 0.23750(17) 0.05394(6) 0.28696(13) 0.0323(3) Uani 1 1 d . . . . .
C8 C 0.19882(16) 0.03888(6) 0.02829(13) 0.0307(3) Uani 1 1 d . . . . .
C9 C 0.28138(18) -0.02001(6) 0.04103(14) 0.0354(3) Uani 1 1 d . . . . .
H9 H 0.326717 -0.040009 0.131268 0.042 Uiso 1 1 calc R U . . .
C10 C 0.29905(17) -0.05100(6) -0.08012(14) 0.0340(3) Uani 1 1 d . . . . .
C11 C 0.3882(2) -0.11083(7) -0.06788(17) 0.0443(3) Uani 1 1 d . . . . .
H11 H 0.431841 -0.131808 0.021262 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4113(2) -0.13820(8) -0.18464(18) 0.0475(4) Uani 1 1 d . . . . .
H12 H 0.471319 -0.177320 -0.174247 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3450(2) -0.10762(8) -0.32040(18) 0.0482(4) Uani 1 1 d . . . . .
H13 H 0.361676 -0.126583 -0.399334 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2562(2) -0.05038(7) -0.33757(16) 0.0440(3) Uani 1 1 d . . . . .
H14 H 0.211921 -0.030716 -0.428215 0.053 Uiso 1 1 calc R U . . .
C15 C 0.23116(17) -0.02068(6) -0.21783(14) 0.0344(3) Uani 1 1 d . . . . .
C16 C 0.14393(18) 0.03932(6) -0.22965(14) 0.0356(3) Uani 1 1 d . . . . .
H16 H 0.097305 0.059557 -0.319547 0.043 Uiso 1 1 calc R U . . .
C17 C 0.12644(16) 0.06835(6) -0.11198(13) 0.0317(3) Uani 1 1 d . . . . .
C18 C -0.1169(2) 0.14325(8) -0.24813(17) 0.0487(4) Uani 1 1 d . . . . .
H18 H -0.180106 0.116180 -0.324655 0.058 Uiso 1 1 calc R U . . .
C19 C -0.1562(2) 0.20609(8) -0.23119(19) 0.0556(4) Uani 1 1 d . . . . .
H19 H -0.249717 0.230617 -0.293158 0.067 Uiso 1 1 calc R U . . .
C20 C -0.0269(3) 0.22537(8) -0.10206(18) 0.0547(4) Uani 1 1 d . . . . .
H20 H -0.021403 0.266386 -0.062294 0.066 Uiso 1 1 calc R U . . .
N1 N 0.18506(15) 0.07320(5) 0.14613(11) 0.0351(3) Uani 1 1 d . . . . .
H1A H 0.137726 0.110952 0.126804 0.042 Uiso 1 1 calc R U . . .
N2 N 0.0888(2) 0.17852(6) -0.04126(14) 0.0509(3) Uani 1 1 d . . . . .
N3 N 0.03027(16) 0.12761(5) -0.13351(12) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.29182(15) -0.00008(5) 0.33024(11) 0.0448(3) 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
C1 C6 1.3851(19) . ?
C1 C2 1.388(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.386(2) . ?
C5 C6 1.3929(19) . ?
C6 C7 1.5009(18) . ?
C7 O1 1.2196(16) . ?
C7 N1 1.3617(16) . ?
C8 C9 1.3731(18) . ?
C8 N1 1.4076(16) . ?
C8 C17 1.4318(17) . ?
C9 C10 1.4162(18) . ?
C10 C11 1.4155(19) . ?
C10 C15 1.4173(18) . ?
C11 C12 1.364(2) . ?
C12 C13 1.403(2) . ?
C13 C14 1.363(2) . ?
C14 C15 1.4180(19) . ?
C15 C16 1.4115(19) . ?
C16 C17 1.3668(18) . ?
C17 N3 1.4256(16) . ?
C18 N3 1.3478(18) . ?
C18 C19 1.363(2) . ?
C19 C20 1.380(2) . ?
C20 N2 1.328(2) . ?
N2 N3 1.3608(16) . ?

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
C6 C1 C2 120.01(14) . . ?
C3 C2 C1 120.24(15) . . ?
C4 C3 C2 119.86(15) . . ?
C3 C4 C5 120.65(15) . . ?
C4 C5 C6 119.65(14) . . ?
C1 C6 C5 119.55(13) . . ?
C1 C6 C7 123.49(12) . . ?
C5 C6 C7 116.94(12) . . ?
O1 C7 N1 124.38(12) . . ?
O1 C7 C6 121.14(11) . . ?
N1 C7 C6 114.47(11) . . ?
C9 C8 N1 123.83(11) . . ?
C9 C8 C17 118.53(11) . . ?
N1 C8 C17 117.62(11) . . ?
C8 C9 C10 121.50(12) . . ?
C11 C10 C9 122.13(12) . . ?
C11 C10 C15 118.25(12) . . ?
C9 C10 C15 119.58(12) . . ?
C12 C11 C10 121.09(14) . . ?
C11 C12 C13 120.32(14) . . ?
C14 C13 C12 120.57(14) . . ?
C13 C14 C15 120.28(14) . . ?
C16 C15 C10 118.23(12) . . ?
C16 C15 C14 122.28(12) . . ?
C10 C15 C14 119.47(13) . . ?
C17 C16 C15 121.50(12) . . ?
C16 C17 N3 118.26(11) . . ?
C16 C17 C8 120.63(12) . . ?
N3 C17 C8 121.09(11) . . ?
N3 C18 C19 107.38(14) . . ?
C18 C19 C20 105.00(14) . . ?
N2 C20 C19 112.10(14) . . ?
C7 N1 C8 127.96(11) . . ?
C20 N2 N3 104.36(13) . . ?
C18 N3 N2 111.17(12) . . ?
C18 N3 C17 126.63(12) . . ?
N2 N3 C17 122.01(11) . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037



