# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_ztta363_0m
_database_code_depnum_ccdc_archive 'CCDC 2423943'
loop_
_audit_author_name
_audit_author_address
'Zhao Taot'
;wuyi university
China
;
_audit_update_record             
;
2025-02-14 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2024-09-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O3'
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27
_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      triclinic
_space_group_IT_number           2
_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                   8.3684(4)
_cell_length_b                   8.5801(4)
_cell_length_c                   8.9751(4)
_cell_angle_alpha                89.554(2)
_cell_angle_beta                 83.754(2)
_cell_angle_gamma                84.365(2)
_cell_volume                     637.50(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.357
_cell_measurement_theta_min      2.385
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1145 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.7820.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7367
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2246
_reflns_number_total             2567
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (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         0.335
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.040
_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)+(0.0525P)²+0.2599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1201
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C6(H6), C8(H8), C13(H13), C7(H7), C10(H10), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.91134(11) 0.80091(12) 0.86254(11) 0.0236(3) Uani 1 1 d . . . . .
O1 O 0.88071(12) 0.50005(12) 0.76831(13) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.35888(12) 0.87148(12) 0.95830(13) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.62862(14) 0.83747(14) 0.89346(13) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.76040(16) 0.59180(16) 0.77923(15) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.78842(16) 0.84130(16) 0.64252(15) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.91163(16) 0.77827(17) 0.53607(16) 0.0223(3) Uani 1 1 d . . . . .
H5 H 0.980566 0.689198 0.560344 0.027 Uiso 1 1 calc R U . . .
C1 C 0.59751(17) 0.54658(16) 0.76080(16) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.77181(16) 0.76901(16) 0.79942(16) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.46096(17) 0.64806(16) 0.80998(16) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.68821(17) 0.97106(17) 0.60542(17) 0.0234(3) Uani 1 1 d . . . . .
H9 H 0.603715 1.014513 0.676772 0.028 Uiso 1 1 calc R U . . .
C15 C 0.47808(16) 0.79496(16) 0.89264(16) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.93361(17) 0.84511(18) 0.39543(16) 0.0250(3) Uani 1 1 d . . . . .
H6 H 1.017530 0.801570 0.323555 0.030 Uiso 1 1 calc R U . . .
C8 C 0.71134(18) 1.03749(17) 0.46401(17) 0.0263(3) Uani 1 1 d . . . . .
H8 H 0.642554 1.126418 0.439129 0.032 Uiso 1 1 calc R U . . .
C13 C 0.30816(17) 0.61002(17) 0.78612(17) 0.0255(3) Uani 1 1 d . . . . .
H13 H 0.215266 0.678448 0.819833 0.031 Uiso 1 1 calc R U . . .
C7 C 0.83419(18) 0.97485(18) 0.35890(17) 0.0260(3) Uani 1 1 d . . . . .
H7 H 0.849892 1.020824 0.262441 0.031 Uiso 1 1 calc R U . . .
C10 C 0.57945(18) 0.40526(17) 0.69136(18) 0.0283(4) Uani 1 1 d . . . . .
H10 H 0.671463 0.334296 0.661070 0.034 Uiso 1 1 calc R U . . .
C12 C 0.29192(18) 0.47183(18) 0.71294(18) 0.0285(4) Uani 1 1 d . . . . .
H12 H 0.187771 0.447066 0.694070 0.034 Uiso 1 1 calc R U . . .
C11 C 0.42704(19) 0.36909(18) 0.66691(19) 0.0310(4) Uani 1 1 d . . . . .
H11 H 0.414536 0.273676 0.618463 0.037 Uiso 1 1 calc R U . . .
C16 C 0.92308(19) 0.7455(2) 1.01257(17) 0.0329(4) Uani 1 1 d . . . . .
H16A H 0.920084 0.631627 1.014945 0.049 Uiso 1 1 calc R U . . .
H16B H 0.832281 0.795129 1.079486 0.049 Uiso 1 1 calc R U . . .
H16C H 1.024893 0.771968 1.045757 0.049 Uiso 1 1 calc R U . . .
H1 H 0.639(2) 0.928(2) 0.938(2) 0.033(5) 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
O3 C3 1.4030(16) . ?
O3 C16 1.4347(18) . ?
O1 C2 1.2113(17) . ?
O2 C15 1.2340(17) . ?
N1 C3 1.4638(17) . ?
N1 C15 1.3463(18) . ?
N1 H1 0.89(2) . ?
C2 C1 1.4799(19) . ?
C2 C3 1.546(2) . ?
C4 C5 1.3973(19) . ?
C4 C3 1.5322(19) . ?
C4 C9 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(2) . ?
C1 C14 1.400(2) . ?
C1 C10 1.396(2) . ?
C14 C15 1.494(2) . ?
C14 C13 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.389(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.385(2) . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.391(2) . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C3 O3 C16 115.72(11) . . ?
C3 N1 H1 115.9(12) . . ?
C15 N1 C3 125.42(12) . . ?
C15 N1 H1 117.1(12) . . ?
O1 C2 C1 123.37(13) . . ?
O1 C2 C3 120.81(12) . . ?
C1 C2 C3 115.59(11) . . ?
C5 C4 C3 118.99(12) . . ?
C9 C4 C5 119.28(13) . . ?
C9 C4 C3 121.68(12) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.25(14) . . ?
C6 C5 H5 119.9 . . ?
C14 C1 C2 119.70(13) . . ?
C10 C1 C2 120.42(13) . . ?
C10 C1 C14 119.86(13) . . ?
O3 C3 N1 109.55(11) . . ?
O3 C3 C2 112.87(11) . . ?
O3 C3 C4 105.14(10) . . ?
N1 C3 C2 109.47(11) . . ?
N1 C3 C4 112.59(11) . . ?
C4 C3 C2 107.19(11) . . ?
C1 C14 C15 120.32(13) . . ?
C13 C14 C1 120.00(13) . . ?
C13 C14 C15 119.65(12) . . ?
C4 C9 H9 120.0 . . ?
C4 C9 C8 120.05(13) . . ?
C8 C9 H9 120.0 . . ?
O2 C15 N1 122.21(13) . . ?
O2 C15 C14 120.86(12) . . ?
N1 C15 C14 116.92(12) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.39(14) . . ?
C7 C6 H6 119.8 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.45(14) . . ?
C7 C8 H8 119.8 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.68(13) . . ?
C12 C13 H13 120.2 . . ?
C6 C7 C8 119.57(14) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C1 C10 H10 120.2 . . ?
C11 C10 C1 119.69(14) . . ?
C11 C10 H10 120.2 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.46(14) . . ?
C11 C12 H12 119.8 . . ?
C10 C11 C12 120.27(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 C2 C1 C14 164.55(14) . . . . ?
O1 C2 C1 C10 -17.1(2) . . . . ?
O1 C2 C3 O3 -24.29(19) . . . . ?
O1 C2 C3 N1 -146.60(13) . . . . ?
O1 C2 C3 C4 91.00(16) . . . . ?
C2 C1 C14 C15 -5.3(2) . . . . ?
C2 C1 C14 C13 176.71(13) . . . . ?
C2 C1 C10 C11 -176.11(14) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C4 C9 C8 C7 0.1(2) . . . . ?
C5 C4 C3 O3 66.26(15) . . . . ?
C5 C4 C3 N1 -174.52(11) . . . . ?
C5 C4 C3 C2 -54.08(15) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C1 C2 C3 O3 160.99(11) . . . . ?
C1 C2 C3 N1 38.68(16) . . . . ?
C1 C2 C3 C4 -83.72(14) . . . . ?
C1 C14 C15 O2 -167.65(14) . . . . ?
C1 C14 C15 N1 11.4(2) . . . . ?
C1 C14 C13 C12 -0.3(2) . . . . ?
C1 C10 C11 C12 -0.9(2) . . . . ?
C3 N1 C15 O2 -169.36(14) . . . . ?
C3 N1 C15 C14 11.6(2) . . . . ?
C3 C2 C1 C14 -20.89(19) . . . . ?
C3 C2 C1 C10 157.51(13) . . . . ?
C3 C4 C5 C6 -177.38(12) . . . . ?
C3 C4 C9 C8 177.23(12) . . . . ?
C14 C1 C10 C11 2.3(2) . . . . ?
C14 C13 C12 C11 1.8(2) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C9 C4 C3 O3 -111.29(13) . . . . ?
C9 C4 C3 N1 7.92(18) . . . . ?
C9 C4 C3 C2 128.36(13) . . . . ?
C9 C8 C7 C6 0.2(2) . . . . ?
C15 N1 C3 O3 -160.18(13) . . . . ?
C15 N1 C3 C2 -35.91(18) . . . . ?
C15 N1 C3 C4 83.21(17) . . . . ?
C15 C14 C13 C12 -178.32(13) . . . . ?
C13 C14 C15 O2 10.4(2) . . . . ?
C13 C14 C15 N1 -170.58(13) . . . . ?
C13 C12 C11 C10 -1.2(3) . . . . ?
C10 C1 C14 C15 176.29(13) . . . . ?
C10 C1 C14 C13 -1.7(2) . . . . ?
C16 O3 C3 N1 58.08(15) . . . . ?
C16 O3 C3 C2 -64.18(15) . . . . ?
C16 O3 C3 C4 179.31(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ??/??/??'
