# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
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data_cu_231217lu_lgpz305784_0m
_database_code_depnum_ccdc_archive 'CCDC 2320411'
loop_
_audit_author_name
_audit_author_address
'Hui Qin'
;Hangzhou Medical College
China
;
_audit_update_record             
;
2023-12-19 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2 O3'
_chemical_formula_sum            'C17 H12 N2 O3'
_chemical_formula_weight         292.29
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.7263(17)
_cell_length_b                   15.850(6)
_cell_length_c                   17.689(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1325.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      61.37
_cell_measurement_theta_min      5.58
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.5981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.7930.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12691
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.262
_diffrn_reflns_theta_min         3.744
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                1383
_reflns_number_total             2499
_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, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 407 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.0106(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.038
_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)+(0.1058P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.2033
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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
O3 O 0.4109(9) 0.5521(3) 0.7730(2) 0.0651(12) Uani 1 1 d . . . . .
O2 O 0.3510(9) 0.3557(3) 0.5414(2) 0.0696(14) Uani 1 1 d . . . . .
O1 O 0.0798(9) 0.4568(3) 0.8037(2) 0.0637(12) Uani 1 1 d . . . . .
N2 N 0.6304(10) 0.5329(3) 0.6382(3) 0.0540(13) Uani 1 1 d . . . . .
H2 H 0.614877 0.560391 0.681234 0.065 Uiso 1 1 calc R U . . .
N3 N 0.7077(11) 0.4444(4) 0.5078(3) 0.0596(15) Uani 1 1 d . . . . .
C1 C 0.8224(11) 0.5637(4) 0.5856(3) 0.0502(15) Uani 1 1 d . . . . .
C2 C 0.9720(12) 0.6370(4) 0.5995(4) 0.0592(17) Uani 1 1 d . . . . .
H2A H 0.941999 0.667337 0.645079 0.071 Uiso 1 1 calc R U . . .
C3 C 1.1653(13) 0.6663(5) 0.5469(4) 0.0663(19) Uani 1 1 d . . . . .
H3 H 1.266765 0.717063 0.555989 0.080 Uiso 1 1 calc R U . . .
C4 C 1.2097(15) 0.6213(5) 0.4812(4) 0.0675(19) Uani 1 1 d . . . . .
H4 H 1.343096 0.641175 0.445187 0.081 Uiso 1 1 calc R U . . .
C5 C 1.0616(13) 0.5473(5) 0.4671(3) 0.0609(17) Uani 1 1 d . . . . .
H5 H 1.094845 0.516737 0.421722 0.073 Uiso 1 1 calc R U . . .
C6 C 0.8649(13) 0.5178(4) 0.5192(3) 0.0531(16) Uani 1 1 d . . . . .
C7 C 0.4998(12) 0.4167(4) 0.5565(3) 0.0564(16) Uani 1 1 d . . . . .
C8 C 0.4657(12) 0.4643(4) 0.6285(3) 0.0499(15) Uani 1 1 d . . . . .
C9 C 0.2795(12) 0.4398(4) 0.6856(3) 0.0505(15) Uani 1 1 d . . . . .
C10 C 0.2738(13) 0.4899(4) 0.7542(3) 0.0551(16) Uani 1 1 d . . . . .
C11 C 0.0762(12) 0.3720(4) 0.6974(3) 0.0534(15) Uani 1 1 d . . . . .
C12 C -0.0374(13) 0.3860(4) 0.7692(4) 0.0557(16) Uani 1 1 d . . . . .
C13 C -0.2390(14) 0.3365(5) 0.8027(4) 0.0660(19) Uani 1 1 d . . . . .
H13 H -0.308894 0.348968 0.851834 0.079 Uiso 1 1 calc R U . . .
C14 C -0.3362(14) 0.2681(5) 0.7626(4) 0.070(2) Uani 1 1 d . . . . .
H14 H -0.474692 0.232024 0.784288 0.085 Uiso 1 1 calc R U . . .
C15 C -0.2338(14) 0.2517(4) 0.6911(4) 0.0682(19) Uani 1 1 d . . . . .
H15 H -0.301927 0.203979 0.664188 0.082 Uiso 1 1 calc R U . . .
C16 C -0.0323(14) 0.3038(4) 0.6577(4) 0.0631(18) Uani 1 1 d . . . . .
H16 H 0.030958 0.292605 0.607703 0.076 Uiso 1 1 calc R U . . .
C17 C 0.7530(16) 0.3927(4) 0.4396(3) 0.075(2) Uani 1 1 d . . . . .
H17A H 0.695828 0.424713 0.394777 0.112 Uiso 1 1 calc R U . . .
H17B H 0.639642 0.341037 0.443128 0.112 Uiso 1 1 calc R U . . .
H17C H 0.953744 0.377806 0.435635 0.112 Uiso 1 1 calc R U . . .


_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
O3 C10 1.226(7) . ?
O2 C7 1.225(7) . ?
O1 C10 1.373(7) . ?
O1 C12 1.393(7) . ?
N2 H2 0.8800 . ?
N2 C1 1.387(7) . ?
N2 C8 1.348(7) . ?
N3 C6 1.395(8) . ?
N3 C7 1.379(7) . ?
N3 C17 1.474(8) . ?
C1 C2 1.382(8) . ?
C1 C6 1.397(8) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(8) . ?
C7 C8 1.489(8) . ?
C8 C9 1.395(8) . ?
C9 C10 1.450(9) . ?
C9 C11 1.457(8) . ?
C11 C12 1.397(8) . ?
C11 C16 1.387(8) . ?
C12 C13 1.369(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(9) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C10 O1 C12 107.1(5) . . ?
C1 N2 H2 117.4 . . ?
C8 N2 H2 117.4 . . ?
C8 N2 C1 125.1(5) . . ?
C6 N3 C17 120.3(5) . . ?
C7 N3 C6 123.7(5) . . ?
C7 N3 C17 116.0(5) . . ?
N2 C1 C6 118.4(6) . . ?
C2 C1 N2 120.8(6) . . ?
C2 C1 C6 120.9(6) . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.1(6) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(7) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(6) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(6) . . ?
C6 C5 H5 119.9 . . ?
N3 C6 C1 118.6(5) . . ?
C5 C6 N3 122.8(6) . . ?
C5 C6 C1 118.6(6) . . ?
O2 C7 N3 121.6(6) . . ?
O2 C7 C8 121.6(5) . . ?
N3 C7 C8 116.8(6) . . ?
N2 C8 C7 117.1(5) . . ?
N2 C8 C9 119.8(5) . . ?
C9 C8 C7 123.1(5) . . ?
C8 C9 C10 117.7(5) . . ?
C8 C9 C11 136.5(6) . . ?
C10 C9 C11 105.8(5) . . ?
O3 C10 O1 119.2(6) . . ?
O3 C10 C9 131.1(6) . . ?
O1 C10 C9 109.7(5) . . ?
C12 C11 C9 105.4(5) . . ?
C16 C11 C9 138.3(6) . . ?
C16 C11 C12 116.2(6) . . ?
O1 C12 C11 112.0(5) . . ?
C13 C12 O1 123.3(6) . . ?
C13 C12 C11 124.8(6) . . ?
C12 C13 H13 121.3 . . ?
C12 C13 C14 117.4(6) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(7) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(7) . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 120.0(6) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 C7 C8 N2 -176.9(5) . . . . ?
O2 C7 C8 C9 4.8(9) . . . . ?
O1 C12 C13 C14 -179.7(6) . . . . ?
N2 C1 C2 C3 179.2(5) . . . . ?
N2 C1 C6 N3 1.6(8) . . . . ?
N2 C1 C6 C5 -178.6(5) . . . . ?
N2 C8 C9 C10 -0.5(8) . . . . ?
N2 C8 C9 C11 -179.2(6) . . . . ?
N3 C7 C8 N2 3.3(8) . . . . ?
N3 C7 C8 C9 -175.0(5) . . . . ?
C1 N2 C8 C7 1.9(8) . . . . ?
C1 N2 C8 C9 -179.8(5) . . . . ?
C1 C2 C3 C4 -0.7(9) . . . . ?
C2 C1 C6 N3 -179.7(5) . . . . ?
C2 C1 C6 C5 0.1(9) . . . . ?
C2 C3 C4 C5 0.3(10) . . . . ?
C3 C4 C5 C6 0.3(9) . . . . ?
C4 C5 C6 N3 179.3(6) . . . . ?
C4 C5 C6 C1 -0.5(9) . . . . ?
C6 N3 C7 O2 174.0(6) . . . . ?
C6 N3 C7 C8 -6.2(8) . . . . ?
C6 C1 C2 C3 0.5(9) . . . . ?
C7 N3 C6 C1 3.8(9) . . . . ?
C7 N3 C6 C5 -176.0(6) . . . . ?
C7 C8 C9 C10 177.7(5) . . . . ?
C7 C8 C9 C11 -0.9(10) . . . . ?
C8 N2 C1 C2 176.8(5) . . . . ?
C8 N2 C1 C6 -4.4(8) . . . . ?
C8 C9 C10 O3 -1.2(10) . . . . ?
C8 C9 C10 O1 -180.0(5) . . . . ?
C8 C9 C11 C12 179.6(6) . . . . ?
C8 C9 C11 C16 -2.9(13) . . . . ?
C9 C11 C12 O1 -0.5(7) . . . . ?
C9 C11 C12 C13 179.8(6) . . . . ?
C9 C11 C16 C15 180.0(7) . . . . ?
C10 O1 C12 C11 -0.1(7) . . . . ?
C10 O1 C12 C13 179.6(6) . . . . ?
C10 C9 C11 C12 0.8(6) . . . . ?
C10 C9 C11 C16 178.4(7) . . . . ?
C11 C9 C10 O3 177.8(6) . . . . ?
C11 C9 C10 O1 -1.0(7) . . . . ?
C11 C12 C13 C14 0.0(10) . . . . ?
C12 O1 C10 O3 -178.3(5) . . . . ?
C12 O1 C10 C9 0.7(7) . . . . ?
C12 C11 C16 C15 -2.7(9) . . . . ?
C12 C13 C14 C15 -0.6(10) . . . . ?
C13 C14 C15 C16 -0.4(10) . . . . ?
C14 C15 C16 C11 2.2(10) . . . . ?
C16 C11 C12 O1 -178.6(5) . . . . ?
C16 C11 C12 C13 1.7(9) . . . . ?
C17 N3 C6 C1 -177.9(6) . . . . ?
C17 N3 C6 C5 2.3(9) . . . . ?
C17 N3 C7 O2 -4.3(9) . . . . ?
C17 N3 C7 C8 175.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
