# Supplementary Information (SI) for Chemical Science.
# 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. 
# 
#######################################################################

data_a_a
_database_code_depnum_ccdc_archive 'CCDC 2479566'
loop_
_audit_author_name
_audit_author_address
ABE
;yanan university 
China
;
_audit_update_record             
;
2025-08-11 deposited with the CCDC.	2026-03-24 downloaded from the CCDC.
;
_audit_creation_date             2025-06-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H29 N3 O2'
_chemical_formula_sum            'C22 H29 N3 O2'
_chemical_formula_weight         367.48
_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      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                   7.6565(2)
_cell_length_b                   10.3732(3)
_cell_length_c                   14.0443(4)
_cell_angle_alpha                100.8520(10)
_cell_angle_beta                 94.3000(10)
_cell_angle_gamma                107.0780(10)
_cell_volume                     1037.05(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      66.61
_cell_measurement_theta_min      4.99
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.8956.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13312
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.702
_diffrn_reflns_theta_max         66.702
_diffrn_reflns_theta_min         6.162
_diffrn_ambient_temperature      213.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_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                3344
_reflns_number_total             3518
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.054
_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)+(0.0457P)²+0.2664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19-C15 \\sim C18-C15
 with sigma of 0.02
 C23-C20 \\sim C22-C20
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C16 \\sim C18 \\sim C19: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C15(H15A,H15B), C20(H20A,H20B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.81375(13) 0.42377(10) 0.55023(7) 0.0495(3) Uani 1 1 d . . . . .
O2 O 0.48331(12) 0.30660(8) 0.27591(7) 0.0442(2) Uani 1 1 d . . . . .
N1 N 0.97678(14) 0.88113(10) 0.34524(8) 0.0439(3) Uani 1 1 d . . . . .
N2 N 0.69727(13) 0.49456(10) 0.42559(7) 0.0371(2) Uani 1 1 d . . . . .
H2 H 0.658540 0.408668 0.393701 0.044 Uiso 1 1 calc R U . . .
N3 N 0.31849(13) 0.37173(10) 0.16511(8) 0.0386(3) Uani 1 1 d . . . . .
C1 C 0.94641(16) 0.78280(12) 0.39084(9) 0.0380(3) Uani 1 1 d . . . . .
H1 H 1.035260 0.739776 0.403492 0.046 Uiso 1 1 calc R U . . .
C2 C 0.81179(17) 0.91860(12) 0.33913(9) 0.0401(3) Uani 1 1 d . . . . .
C3 C 0.7815(2) 1.02025(13) 0.29505(11) 0.0529(4) Uani 1 1 d . . . . .
H3 H 0.873371 1.073463 0.264864 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6108(2) 1.04060(14) 0.29713(12) 0.0604(4) Uani 1 1 d . . . . .
H4 H 0.586238 1.108994 0.267891 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4758(2) 0.96202(15) 0.34147(12) 0.0583(4) Uani 1 1 d . . . . .
H5 H 0.361022 0.977855 0.341708 0.070 Uiso 1 1 calc R U . . .
C6 C 0.50668(19) 0.86004(13) 0.38571(11) 0.0481(3) Uani 1 1 d . . . . .
H6 H 0.415031 0.807067 0.416126 0.058 Uiso 1 1 calc R U . . .
C7 C 0.67681(16) 0.83910(11) 0.38348(9) 0.0372(3) Uani 1 1 d . . . . .
C8 C 0.75545(15) 0.74001(11) 0.42339(9) 0.0339(3) Uani 1 1 d . . . . .
C9 C 0.76779(18) 0.76125(13) 0.53564(9) 0.0418(3) Uani 1 1 d . . . . .
H9A H 0.837399 0.857772 0.566046 0.050 Uiso 1 1 calc R U . . .
H9B H 0.643311 0.742206 0.554099 0.050 Uiso 1 1 calc R U . . .
C10 C 0.86168(19) 0.66682(13) 0.57359(9) 0.0440(3) Uani 1 1 d . . . . .
H10A H 0.994387 0.702602 0.571050 0.053 Uiso 1 1 calc R U . . .
H10B H 0.844742 0.669513 0.642332 0.053 Uiso 1 1 calc R U . . .
C11 C 0.79080(16) 0.51949(13) 0.51756(9) 0.0386(3) Uani 1 1 d . . . . .
C12 C 0.65651(15) 0.58871(11) 0.37688(9) 0.0322(3) Uani 1 1 d . . . . .
C13 C 0.54042(15) 0.54732(11) 0.29228(9) 0.0345(3) Uani 1 1 d . . . . .
H13 H 0.517832 0.615472 0.262062 0.041 Uiso 1 1 calc R U . . .
C14 C 0.44728(15) 0.40194(11) 0.24467(9) 0.0354(3) Uani 1 1 d . . . . .
C15 C 0.23364(17) 0.22551(13) 0.11682(11) 0.0466(3) Uani 1 1 d D . . . .
H15A H 0.116749 0.214601 0.077590 0.056 Uiso 1 1 calc R U . . .
H15B H 0.205410 0.171448 0.167086 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3541(2) 0.16678(14) 0.05068(12) 0.0556(4) Uani 1 1 d . U . . .
C18 C 0.2611(3) 0.01330(18) 0.01063(19) 0.0900(7) Uani 1 1 d D U . . .
H18A H 0.235240 -0.032606 0.064486 0.135 Uiso 1 1 calc R U . . .
H18B H 0.342074 -0.024607 -0.027634 0.135 Uiso 1 1 calc R U . . .
H18C H 0.146599 -0.001163 -0.030617 0.135 Uiso 1 1 calc R U . . .
C19 C 0.3989(4) 0.2424(2) -0.03088(16) 0.0959(7) Uani 1 1 d D U . . .
H19A H 0.285678 0.232117 -0.071750 0.144 Uiso 1 1 calc R U . . .
H19B H 0.478122 0.203831 -0.070138 0.144 Uiso 1 1 calc R U . . .
H19C H 0.461804 0.339674 -0.003104 0.144 Uiso 1 1 calc R U . . .
C20 C 0.25602(18) 0.47570(13) 0.12823(9) 0.0418(3) Uani 1 1 d D . . . .
H20A H 0.199932 0.437046 0.059809 0.050 Uiso 1 1 calc R U . . .
H20B H 0.363937 0.555569 0.129340 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1176(2) 0.52583(16) 0.18494(10) 0.0529(4) Uani 1 1 d . . . . .
C22 C -0.0627(2) 0.4112(2) 0.17821(14) 0.0758(5) Uani 1 1 d D . . . .
H22A H -0.121096 0.379224 0.110648 0.114 Uiso 1 1 calc R U . . .
H22B H -0.143937 0.446050 0.218195 0.114 Uiso 1 1 calc R U . . .
H22C H -0.038398 0.334975 0.201482 0.114 Uiso 1 1 calc R U . . .
C23 C 0.0896(3) 0.6484(2) 0.14771(13) 0.0808(6) Uani 1 1 d D . . . .
H23A H 0.204738 0.724041 0.161695 0.121 Uiso 1 1 calc R U . . .
H23B H -0.003948 0.678070 0.180180 0.121 Uiso 1 1 calc R U . . .
H23C H 0.050167 0.621070 0.077609 0.121 Uiso 1 1 calc R U . . .
H21 H 0.173(2) 0.5580(16) 0.2537(12) 0.053(4) Uiso 1 1 d . . . . .
H16 H 0.467(3) 0.1799(17) 0.0916(12) 0.058(4) 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 C11 1.2203(14) . ?
O2 C14 1.2458(14) . ?
N1 C1 1.2782(16) . ?
N1 C2 1.4279(16) . ?
N2 H2 0.8700 . ?
N2 C11 1.3693(16) . ?
N2 C12 1.3848(14) . ?
N3 C14 1.3567(16) . ?
N3 C15 1.4664(15) . ?
N3 C20 1.4617(15) . ?
C1 H1 0.9400 . ?
C1 C8 1.5294(16) . ?
C2 C3 1.3844(18) . ?
C2 C7 1.3876(18) . ?
C3 H3 0.9400 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.3837(18) . ?
C7 C8 1.5044(15) . ?
C8 C9 1.5418(17) . ?
C8 C12 1.5183(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.5208(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C11 1.4985(18) . ?
C12 C13 1.3459(16) . ?
C13 H13 0.9400 . ?
C13 C14 1.4653(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 C16 1.526(2) . ?
C16 C18 1.515(2) . ?
C16 C19 1.511(3) . ?
C16 H16 0.960(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 C21 1.5237(18) . ?
C21 C22 1.518(3) . ?
C21 C23 1.527(2) . ?
C21 H21 0.979(17) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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
C1 N1 C2 106.35(10) . . ?
C11 N2 H2 115.9 . . ?
C11 N2 C12 128.23(10) . . ?
C12 N2 H2 115.9 . . ?
C14 N3 C15 117.25(10) . . ?
C14 N3 C20 123.65(10) . . ?
C20 N3 C15 119.05(10) . . ?
N1 C1 H1 122.3 . . ?
N1 C1 C8 115.34(10) . . ?
C8 C1 H1 122.3 . . ?
C3 C2 N1 126.48(12) . . ?
C3 C2 C7 121.68(12) . . ?
C7 C2 N1 111.84(10) . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.48(14) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.16(13) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.20(13) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.80(14) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C8 107.60(10) . . ?
C6 C7 C2 120.68(12) . . ?
C6 C7 C8 131.71(12) . . ?
C1 C8 C9 111.75(10) . . ?
C7 C8 C1 98.87(9) . . ?
C7 C8 C9 113.11(9) . . ?
C7 C8 C12 114.31(9) . . ?
C12 C8 C1 109.31(9) . . ?
C12 C8 C9 109.14(9) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.33(10) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.98(10) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
O1 C11 N2 119.97(11) . . ?
O1 C11 C10 122.99(11) . . ?
N2 C11 C10 117.05(10) . . ?
N2 C12 C8 115.72(9) . . ?
C13 C12 N2 121.58(10) . . ?
C13 C12 C8 122.67(10) . . ?
C12 C13 H13 118.2 . . ?
C12 C13 C14 123.65(10) . . ?
C14 C13 H13 118.2 . . ?
O2 C14 N3 119.80(10) . . ?
O2 C14 C13 121.50(10) . . ?
N3 C14 C13 118.70(10) . . ?
N3 C15 H15A 108.8 . . ?
N3 C15 H15B 108.8 . . ?
N3 C15 C16 113.94(11) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16 106.2(10) . . ?
C18 C16 C15 109.89(13) . . ?
C18 C16 H16 108.8(10) . . ?
C19 C16 C15 111.92(14) . . ?
C19 C16 C18 111.28(17) . . ?
C19 C16 H16 108.6(10) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 108.5 . . ?
N3 C20 H20B 108.5 . . ?
N3 C20 C21 114.96(11) . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C20 C21 C23 108.36(13) . . ?
C20 C21 H21 107.0(9) . . ?
C22 C21 C20 112.17(13) . . ?
C22 C21 C23 112.21(14) . . ?
C22 C21 H21 108.3(9) . . ?
C23 C21 H21 108.6(9) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
N1 C1 C8 C7 0.70(13) . . . . ?
N1 C1 C8 C9 -118.64(12) . . . . ?
N1 C1 C8 C12 120.45(11) . . . . ?
N1 C2 C3 C4 -179.98(13) . . . . ?
N1 C2 C7 C6 179.71(11) . . . . ?
N1 C2 C7 C8 0.25(14) . . . . ?
N2 C12 C13 C14 0.25(18) . . . . ?
N3 C15 C16 C18 175.63(15) . . . . ?
N3 C15 C16 C19 -60.19(18) . . . . ?
N3 C20 C21 C22 -64.22(15) . . . . ?
N3 C20 C21 C23 171.36(12) . . . . ?
C1 N1 C2 C3 -179.54(12) . . . . ?
C1 N1 C2 C7 0.20(14) . . . . ?
C1 C8 C9 C10 -65.00(13) . . . . ?
C1 C8 C12 N2 84.04(12) . . . . ?
C1 C8 C12 C13 -94.11(13) . . . . ?
C2 N1 C1 C8 -0.58(14) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C7 C8 C1 -0.51(12) . . . . ?
C2 C7 C8 C9 117.81(11) . . . . ?
C2 C7 C8 C12 -116.46(11) . . . . ?
C3 C2 C7 C6 -0.54(19) . . . . ?
C3 C2 C7 C8 180.00(11) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C2 0.54(19) . . . . ?
C5 C6 C7 C8 179.85(12) . . . . ?
C6 C7 C8 C1 -179.89(13) . . . . ?
C6 C7 C8 C9 -61.57(17) . . . . ?
C6 C7 C8 C12 64.16(17) . . . . ?
C7 C2 C3 C4 0.30(19) . . . . ?
C7 C8 C9 C10 -175.53(10) . . . . ?
C7 C8 C12 N2 -166.24(10) . . . . ?
C7 C8 C12 C13 15.61(16) . . . . ?
C8 C9 C10 C11 -47.18(15) . . . . ?
C8 C12 C13 C14 178.29(10) . . . . ?
C9 C8 C12 N2 -38.46(13) . . . . ?
C9 C8 C12 C13 143.39(11) . . . . ?
C9 C10 C11 O1 -161.07(12) . . . . ?
C9 C10 C11 N2 19.22(16) . . . . ?
C11 N2 C12 C8 11.69(17) . . . . ?
C11 N2 C12 C13 -170.14(12) . . . . ?
C12 N2 C11 O1 179.36(11) . . . . ?
C12 N2 C11 C10 -0.92(18) . . . . ?
C12 C8 C9 C10 56.01(13) . . . . ?
C12 C13 C14 O2 -6.47(18) . . . . ?
C12 C13 C14 N3 173.20(11) . . . . ?
C14 N3 C15 C16 -78.65(16) . . . . ?
C14 N3 C20 C21 -78.47(15) . . . . ?
C15 N3 C14 O2 -2.84(17) . . . . ?
C15 N3 C14 C13 177.49(10) . . . . ?
C15 N3 C20 C21 98.99(13) . . . . ?
C20 N3 C14 O2 174.66(11) . . . . ?
C20 N3 C14 C13 -5.01(17) . . . . ?
C20 N3 C15 C16 103.73(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2479567'
loop_
_audit_author_name
_audit_author_address
ABSD
;yanan university 
China
;
_audit_update_record             
;
2025-08-11 deposited with the CCDC.	2026-03-24 downloaded from the CCDC.
;
_audit_creation_date             2025-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 N2 O3'
_chemical_formula_sum            'C17 H18 N2 O3'
_chemical_formula_weight         298.33
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.1923(8)
_cell_length_b                   12.3323(10)
_cell_length_c                   13.0563(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.121(3)
_cell_angle_gamma                90
_cell_volume                     1550.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    243.00
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.58
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0499 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.9118.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10025
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         5.829
_diffrn_ambient_temperature      243.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_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                2539
_reflns_number_total             2642
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.188
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.056
_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)+(0.0547P)²+0.3713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
;
_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
O1 O 0.47537(10) 0.51472(8) 0.12470(9) 0.0521(3) Uani 1 1 d . . . . .
O2 O 0.62257(9) 0.63684(9) 0.22743(9) 0.0552(3) Uani 1 1 d . . . . .
O3 O 0.62962(10) 0.91058(10) 0.42567(8) 0.0579(3) Uani 1 1 d . . . . .
N2 N 0.50014(11) 0.80808(10) 0.28841(9) 0.0423(3) Uani 1 1 d . . . . .
N1 N 0.02336(11) 0.77268(10) 0.09215(9) 0.0461(3) Uani 1 1 d . . . . .
C6 C 0.16629(12) 0.75839(10) 0.27307(10) 0.0343(3) Uani 1 1 d . . . . .
C14 C 0.37946(12) 0.76550(10) 0.21738(10) 0.0345(3) Uani 1 1 d . . . . .
C8 C 0.24507(12) 0.82213(10) 0.21216(10) 0.0355(3) Uani 1 1 d . . . . .
C15 C 0.38069(13) 0.67521(11) 0.15954(10) 0.0383(3) Uani 1 1 d . . . . .
C7 C 0.19935(13) 0.72535(10) 0.37949(10) 0.0380(3) Uani 1 1 d . . . . .
H7 H 0.287273 0.740624 0.429728 0.046 Uiso 1 1 calc R U . . .
C9 C 0.13742(13) 0.82027(11) 0.09827(10) 0.0413(3) Uani 1 1 d . . . . .
C5 C 0.03730(12) 0.73296(11) 0.19757(11) 0.0393(3) Uani 1 1 d . . . . .
C16 C 0.50491(13) 0.61065(11) 0.17430(10) 0.0395(3) Uani 1 1 d . . . . .
C3 C -0.02772(14) 0.64451(11) 0.33493(13) 0.0488(4) Uani 1 1 d . . . . .
H3 H -0.093801 0.606097 0.356648 0.059 Uiso 1 1 calc R U . . .
C4 C -0.06053(14) 0.67526(12) 0.22751(12) 0.0480(3) Uani 1 1 d . . . . .
H4 H -0.146884 0.657400 0.176404 0.058 Uiso 1 1 calc R U . . .
C2 C 0.10019(14) 0.66871(11) 0.41182(11) 0.0433(3) Uani 1 1 d . . . . .
C13 C 0.51486(14) 0.88986(11) 0.36296(11) 0.0426(3) Uani 1 1 d . . . . .
C11 C 0.27366(14) 0.94074(11) 0.25072(11) 0.0437(3) Uani 1 1 d . . . . .
H11A H 0.302919 0.982016 0.197800 0.052 Uiso 1 1 calc R U . . .
H11B H 0.187867 0.973388 0.254842 0.052 Uiso 1 1 calc R U . . .
C12 C 0.38545(14) 0.94788(11) 0.36087(11) 0.0452(3) Uani 1 1 d . . . . .
H12A H 0.407220 1.024278 0.379425 0.054 Uiso 1 1 calc R U . . .
H12B H 0.350296 0.916401 0.415734 0.054 Uiso 1 1 calc R U . . .
C1 C 0.13144(19) 0.63718(14) 0.52924(13) 0.0601(4) Uani 1 1 d . . . . .
H1A H 0.229844 0.622106 0.561428 0.090 Uiso 1 1 calc R U . . .
H1B H 0.078590 0.572962 0.533621 0.090 Uiso 1 1 calc R U . . .
H1C H 0.105965 0.696238 0.568057 0.090 Uiso 1 1 calc R U . . .
C10 C 0.16122(19) 0.87426(15) 0.00378(13) 0.0629(4) Uani 1 1 d . . . . .
H10A H 0.079159 0.866379 -0.059644 0.094 Uiso 1 1 calc R U . . .
H10B H 0.239962 0.840885 -0.010037 0.094 Uiso 1 1 calc R U . . .
H10C H 0.180025 0.950665 0.019496 0.094 Uiso 1 1 calc R U . . .
C17 C 0.59178(18) 0.44278(14) 0.13822(16) 0.0656(5) Uani 1 1 d . . . . .
H17A H 0.655133 0.475003 0.105330 0.098 Uiso 1 1 calc R U . . .
H17B H 0.558541 0.373904 0.103527 0.098 Uiso 1 1 calc R U . . .
H17C H 0.639800 0.431148 0.214877 0.098 Uiso 1 1 calc R U . . .
H2 H 0.5773(19) 0.7701(15) 0.2911(14) 0.064(5) Uiso 1 1 d . . . . .
H15 H 0.2961(16) 0.6494(12) 0.1097(12) 0.042(4) 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 C16 1.3347(17) . ?
O1 C17 1.4453(18) . ?
O2 C16 1.2160(16) . ?
O3 C13 1.2151(16) . ?
N2 C14 1.3789(16) . ?
N2 C13 1.3753(18) . ?
N2 H2 0.906(19) . ?
N1 C9 1.2812(18) . ?
N1 C5 1.4235(18) . ?
C6 C8 1.5210(17) . ?
C6 C7 1.3796(18) . ?
C6 C5 1.3963(17) . ?
C14 C8 1.5189(17) . ?
C14 C15 1.3478(18) . ?
C8 C9 1.5319(17) . ?
C8 C11 1.5434(18) . ?
C15 C16 1.4541(18) . ?
C15 H15 0.950(16) . ?
C7 H7 0.9400 . ?
C7 C2 1.4025(18) . ?
C9 C10 1.490(2) . ?
C5 C4 1.3816(19) . ?
C3 H3 0.9400 . ?
C3 C4 1.384(2) . ?
C3 C2 1.393(2) . ?
C4 H4 0.9400 . ?
C2 C1 1.511(2) . ?
C13 C12 1.493(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C12 1.5168(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?

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
C16 O1 C17 116.05(12) . . ?
C14 N2 H2 113.7(11) . . ?
C13 N2 C14 128.44(11) . . ?
C13 N2 H2 117.3(11) . . ?
C9 N1 C5 107.23(10) . . ?
C7 C6 C8 133.05(11) . . ?
C7 C6 C5 120.50(11) . . ?
C5 C6 C8 106.45(11) . . ?
N2 C14 C8 116.60(11) . . ?
C15 C14 N2 121.43(11) . . ?
C15 C14 C8 121.90(11) . . ?
C6 C8 C9 99.61(10) . . ?
C6 C8 C11 113.25(10) . . ?
C14 C8 C6 111.20(10) . . ?
C14 C8 C9 112.66(10) . . ?
C14 C8 C11 110.49(10) . . ?
C9 C8 C11 109.24(10) . . ?
C14 C15 C16 123.07(12) . . ?
C14 C15 H15 119.2(9) . . ?
C16 C15 H15 117.6(9) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C2 119.20(12) . . ?
C2 C7 H7 120.4 . . ?
N1 C9 C8 114.47(11) . . ?
N1 C9 C10 122.92(13) . . ?
C10 C9 C8 122.54(12) . . ?
C6 C5 N1 112.21(11) . . ?
C4 C5 N1 126.74(12) . . ?
C4 C5 C6 121.05(13) . . ?
O1 C16 C15 111.88(11) . . ?
O2 C16 O1 122.40(12) . . ?
O2 C16 C15 125.68(12) . . ?
C4 C3 H3 119.0 . . ?
C4 C3 C2 122.02(12) . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 118.08(12) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C7 C2 C1 120.02(13) . . ?
C3 C2 C7 119.11(13) . . ?
C3 C2 C1 120.85(13) . . ?
O3 C13 N2 119.27(13) . . ?
O3 C13 C12 124.14(12) . . ?
N2 C13 C12 116.59(11) . . ?
C8 C11 H11A 109.3 . . ?
C8 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C8 111.54(11) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 111.98(11) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 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
O3 C13 C12 C11 155.68(14) . . . . ?
N2 C14 C8 C6 -103.22(12) . . . . ?
N2 C14 C8 C9 145.93(11) . . . . ?
N2 C14 C8 C11 23.44(15) . . . . ?
N2 C14 C15 C16 5.9(2) . . . . ?
N2 C13 C12 C11 -24.42(17) . . . . ?
N1 C5 C4 C3 -179.39(13) . . . . ?
C6 C8 C9 N1 2.02(14) . . . . ?
C6 C8 C9 C10 179.12(13) . . . . ?
C6 C8 C11 C12 73.03(13) . . . . ?
C6 C7 C2 C3 1.85(19) . . . . ?
C6 C7 C2 C1 -176.66(12) . . . . ?
C6 C5 C4 C3 0.8(2) . . . . ?
C14 N2 C13 O3 173.64(13) . . . . ?
C14 N2 C13 C12 -6.3(2) . . . . ?
C14 C8 C9 N1 119.93(12) . . . . ?
C14 C8 C9 C10 -62.96(17) . . . . ?
C14 C8 C11 C12 -52.48(14) . . . . ?
C14 C15 C16 O1 167.30(12) . . . . ?
C14 C15 C16 O2 -10.6(2) . . . . ?
C8 C6 C7 C2 178.27(12) . . . . ?
C8 C6 C5 N1 0.61(14) . . . . ?
C8 C6 C5 C4 -179.56(12) . . . . ?
C8 C14 C15 C16 -170.95(11) . . . . ?
C8 C11 C12 C13 53.38(15) . . . . ?
C15 C14 C8 C6 73.73(15) . . . . ?
C15 C14 C8 C9 -37.12(16) . . . . ?
C15 C14 C8 C11 -159.61(12) . . . . ?
C7 C6 C8 C14 59.39(17) . . . . ?
C7 C6 C8 C9 178.39(13) . . . . ?
C7 C6 C8 C11 -65.74(17) . . . . ?
C7 C6 C5 N1 -179.22(11) . . . . ?
C7 C6 C5 C4 0.61(19) . . . . ?
C9 N1 C5 C6 0.68(15) . . . . ?
C9 N1 C5 C4 -179.13(14) . . . . ?
C9 C8 C11 C12 -176.95(10) . . . . ?
C5 N1 C9 C8 -1.74(15) . . . . ?
C5 N1 C9 C10 -178.83(14) . . . . ?
C5 C6 C8 C14 -120.42(11) . . . . ?
C5 C6 C8 C9 -1.42(12) . . . . ?
C5 C6 C8 C11 114.46(11) . . . . ?
C5 C6 C7 C2 -1.94(18) . . . . ?
C4 C3 C2 C7 -0.4(2) . . . . ?
C4 C3 C2 C1 178.06(14) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C13 N2 C14 C8 6.4(2) . . . . ?
C13 N2 C14 C15 -170.59(13) . . . . ?
C11 C8 C9 N1 -116.88(13) . . . . ?
C11 C8 C9 C10 60.23(17) . . . . ?
C17 O1 C16 O2 0.34(19) . . . . ?
C17 O1 C16 C15 -177.67(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2498755'
loop_
_audit_author_name
_audit_author_address
'zhiqiang ren'
;Yan an University
China
;
_audit_update_record             
;
2025-10-29 deposited with the CCDC.	2026-03-24 downloaded from the CCDC.
;
_audit_creation_date             2025-10-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H39 Cu N2 O2'
_chemical_formula_sum            'C31 H39 Cu N2 O2'
_chemical_formula_weight         535.18
_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'
Cu Cu -1.9646 0.5888 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.4903(7)
_cell_length_b                   12.6689(7)
_cell_length_c                   22.1306(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.773(2)
_cell_angle_gamma                90
_cell_volume                     3501.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      4.02
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5613
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1028 before and 0.0679 after correction.
The Ratio of minimum to maximum transmission is 0.7453.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.015
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27534
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.021
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5546
_reflns_number_total             6111
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         1.804
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6111
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      1.141
_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)+(0.3500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3720
_refine_ls_wR_factor_ref         0.3873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
C17 \\sim C19 \\sim C18: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
C29 \\sim C30 \\sim C31: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
2.a Riding coordinates:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C19(H19A,H19B,
 H19C), C18(H18A,H18B,H18C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C27(H27A,
 H27B,H27C), C28(H28A,H28B,H28C)
2.b Ternary CH refined with riding coordinates:
 C17(H17), C14(H14), C29(H29), C26(H26)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C24(H24), C23(H23), C22(H22)
;
_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
Cu1 Cu 0.25708(3) 0.23219(4) 0.31077(2) 0.0321(3) Uani 1 1 d . . . . .
O1 O 0.6118(4) 0.1022(7) 0.2087(3) 0.130(2) Uani 1 1 d . . . . .
O2 O 0.6867(5) 0.1718(10) 0.2883(4) 0.187(5) Uani 1 1 d . . . . .
N1 N 0.0064(5) 0.2367(5) 0.3005(3) 0.0808(15) Uani 1 1 d . . . . .
N2 N 0.0630(4) 0.3122(6) 0.3815(2) 0.0914(17) Uani 1 1 d . . . . .
C17 C 0.1154(7) 0.5318(8) 0.3849(3) 0.118(2) Uani 1 1 d . U . . .
H17 H 0.061733 0.494162 0.359682 0.142 Uiso 1 1 calc R U . . .
C1 C 0.7180(7) 0.0756(16) 0.1868(5) 0.185(8) Uani 1 1 d . . . . .
H1A H 0.721093 0.095880 0.144557 0.278 Uiso 1 1 d R U . . .
H1B H 0.729803 0.000180 0.190427 0.278 Uiso 1 1 d R U . . .
H1C H 0.773053 0.113100 0.209497 0.278 Uiso 1 1 d R U . . .
C2 C 0.6093(5) 0.1534(6) 0.2576(3) 0.0893(17) Uani 1 1 d . . . . .
C3 C 0.5051(5) 0.1782(6) 0.2778(3) 0.0879(17) Uani 1 1 d . . . . .
C4 C 0.4131(6) 0.2029(7) 0.2918(3) 0.0876(17) Uani 1 1 d . . . . .
C5 C 0.0969(5) 0.2610(5) 0.3316(3) 0.0709(15) Uani 1 1 d . . . . .
C6 C -0.0813(6) 0.2688(7) 0.3310(4) 0.104(3) Uani 1 1 d . . . . .
H6 H -0.153003 0.263032 0.317996 0.124 Uiso 1 1 calc R U . . .
C7 C -0.0466(6) 0.3092(9) 0.3820(4) 0.109(3) Uani 1 1 d . . . . .
H7 H -0.089862 0.332438 0.413774 0.131 Uiso 1 1 calc R U . . .
C8 C 0.1345(5) 0.3479(7) 0.4306(3) 0.0871(19) Uani 1 1 d . . . . .
C9 C 0.1613(5) 0.4531(7) 0.4299(3) 0.0876(18) Uani 1 1 d . . . . .
C10 C 0.2283(5) 0.4882(7) 0.4762(3) 0.096(2) Uani 1 1 d . . . . .
H10 H 0.244482 0.560547 0.478811 0.115 Uiso 1 1 calc R U . . .
C11 C 0.2707(7) 0.4218(9) 0.5176(3) 0.119(3) Uani 1 1 d . . . . .
H11 H 0.315863 0.447930 0.548474 0.143 Uiso 1 1 calc R U . . .
C12 C 0.2464(8) 0.3088(10) 0.5144(4) 0.125(3) Uani 1 1 d . . . . .
H12 H 0.279186 0.260127 0.540817 0.149 Uiso 1 1 calc R U . . .
C13 C 0.1739(7) 0.2774(6) 0.4711(3) 0.090(2) Uani 1 1 d . . . . .
C14 C 0.1433(9) 0.1580(9) 0.4695(5) 0.130(3) Uani 1 1 d . . . . .
H14 H 0.095342 0.145847 0.434193 0.156 Uiso 1 1 calc R U . . .
C15 C 0.0815(17) 0.1348(17) 0.5262(6) 0.223(9) Uani 1 1 d . . . . .
H15A H 0.119185 0.162181 0.561508 0.335 Uiso 1 1 d R U . . .
H15B H 0.074175 0.058811 0.529908 0.335 Uiso 1 1 d R U . . .
H15C H 0.011115 0.166791 0.523318 0.335 Uiso 1 1 d R U . . .
C16 C 0.2347(11) 0.0870(10) 0.4648(7) 0.166(5) Uani 1 1 d . . . . .
H16A H 0.273604 0.105556 0.428711 0.249 Uiso 1 1 d R U . . .
H16B H 0.212154 0.013836 0.462351 0.249 Uiso 1 1 d R U . . .
H16C H 0.280654 0.096646 0.500051 0.249 Uiso 1 1 d R U . . .
C19 C 0.2064(10) 0.5718(14) 0.3417(5) 0.161(4) Uani 1 1 d . U . . .
H19A H 0.217417 0.646715 0.348569 0.242 Uiso 1 1 d R U . . .
H19B H 0.181117 0.560605 0.300619 0.242 Uiso 1 1 d R U . . .
H19C H 0.273397 0.534525 0.348089 0.242 Uiso 1 1 d R U . . .
C18 C 0.0608(11) 0.6251(11) 0.4125(5) 0.147(3) Uani 1 1 d . U . . .
H18A H 0.006514 0.594981 0.438253 0.220 Uiso 1 1 d R U . . .
H18B H 0.026704 0.667971 0.381413 0.220 Uiso 1 1 d R U . . .
H18C H 0.108894 0.668661 0.436543 0.220 Uiso 1 1 d R U . . .
C20 C 0.0072(4) 0.1790(5) 0.2434(3) 0.0794(16) Uani 1 1 d . . . . .
C25 C 0.0052(4) 0.0672(5) 0.2466(3) 0.0784(14) Uani 1 1 d . . . . .
C24 C 0.0070(5) 0.0129(6) 0.1919(3) 0.0930(18) Uani 1 1 d . . . . .
H24 H 0.008205 -0.061255 0.191640 0.112 Uiso 1 1 calc R U . . .
C23 C 0.0071(5) 0.0682(6) 0.1377(3) 0.0927(19) Uani 1 1 d . . . . .
H23 H 0.009211 0.031467 0.100783 0.111 Uiso 1 1 calc R U . . .
C22 C 0.0042(5) 0.1763(6) 0.1380(3) 0.0835(16) Uani 1 1 d . . . . .
H22 H 0.001339 0.212503 0.100993 0.100 Uiso 1 1 calc R U . . .
C21 C 0.0053(6) 0.2336(5) 0.1909(3) 0.0752(16) Uani 1 1 d . . . . .
C29 C 0.0023(6) 0.3535(6) 0.1881(4) 0.107(2) Uani 1 1 d . U . . .
H29 H -0.003434 0.379349 0.230144 0.128 Uiso 1 1 calc R U . . .
C30 C 0.1032(9) 0.3970(9) 0.1635(6) 0.141(3) Uani 1 1 d . U . . .
H30A H 0.161616 0.350234 0.174861 0.212 Uiso 1 1 d R U . . .
H30B H 0.117276 0.467074 0.179381 0.212 Uiso 1 1 d R U . . .
H30C H 0.097116 0.400264 0.119801 0.212 Uiso 1 1 d R U . . .
C31 C -0.0950(8) 0.3937(8) 0.1536(6) 0.134(3) Uani 1 1 d . U . . .
H31A H -0.084247 0.382530 0.110704 0.201 Uiso 1 1 d R U . . .
H31B H -0.104657 0.468410 0.161274 0.201 Uiso 1 1 d R U . . .
H31C H -0.158127 0.355410 0.166214 0.201 Uiso 1 1 d R U . . .
C26 C 0.0037(7) 0.0064(8) 0.3051(4) 0.109(2) Uani 1 1 d . . . . .
H26 H -0.006552 0.056305 0.338925 0.131 Uiso 1 1 calc R U . . .
C27 C 0.1069(9) -0.0536(10) 0.3152(5) 0.133(3) Uani 1 1 d . . . . .
H27A H 0.103923 -0.117716 0.291285 0.200 Uiso 1 1 d R U . . .
H27B H 0.116803 -0.071646 0.357545 0.200 Uiso 1 1 d R U . . .
H27C H 0.166383 -0.010396 0.302125 0.200 Uiso 1 1 d R U . . .
C28 C -0.0918(13) -0.0741(16) 0.3034(9) 0.249(12) Uani 1 1 d . . . . .
H28A H -0.149141 -0.046513 0.277953 0.374 Uiso 1 1 d R U . . .
H28B H -0.117441 -0.083213 0.344233 0.374 Uiso 1 1 d R U . . .
H28C H -0.068451 -0.141633 0.287703 0.374 Uiso 1 1 d 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
Cu1 C4 2.033(8) . ?
Cu1 C5 2.091(7) . ?
O1 C1 1.458(11) . ?
O1 C2 1.263(8) . ?
O2 C2 1.197(9) . ?
N1 C5 1.350(9) . ?
N1 C6 1.356(10) . ?
N1 C20 1.460(8) . ?
N2 C5 1.353(8) . ?
N2 C7 1.370(9) . ?
N2 C8 1.469(7) . ?
C17 H17 0.9900 . ?
C17 C9 1.516(11) . ?
C17 C19 1.578(15) . ?
C17 C18 1.498(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9702 . ?
C1 H1C 0.9702 . ?
C2 C3 1.417(9) . ?
C3 C4 1.234(10) . ?
C6 H6 0.9400 . ?
C6 C7 1.308(11) . ?
C7 H7 0.9400 . ?
C8 C9 1.374(12) . ?
C8 C13 1.355(11) . ?
C9 C10 1.387(9) . ?
C10 H10 0.9400 . ?
C10 C11 1.347(12) . ?
C11 H11 0.9400 . ?
C11 C12 1.465(16) . ?
C12 H12 0.9400 . ?
C12 C13 1.368(12) . ?
C13 C14 1.560(14) . ?
C14 H14 0.9900 . ?
C14 C15 1.512(17) . ?
C14 C16 1.457(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9701 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9702 . ?
C16 H16B 0.9701 . ?
C16 H16C 0.9698 . ?
C19 H19A 0.9702 . ?
C19 H19B 0.9698 . ?
C19 H19C 0.9700 . ?
C18 H18A 0.9701 . ?
C18 H18B 0.9698 . ?
C18 H18C 0.9701 . ?
C20 C25 1.419(10) . ?
C20 C21 1.353(10) . ?
C25 C24 1.393(9) . ?
C25 C26 1.506(10) . ?
C24 H24 0.9400 . ?
C24 C23 1.389(11) . ?
C23 H23 0.9400 . ?
C23 C22 1.370(10) . ?
C22 H22 0.9400 . ?
C22 C21 1.376(9) . ?
C21 C29 1.520(10) . ?
C29 H29 0.9900 . ?
C29 C30 1.485(13) . ?
C29 C31 1.515(12) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9704 . ?
C30 H30C 0.9700 . ?
C31 H31A 0.9701 . ?
C31 H31B 0.9699 . ?
C31 H31C 0.9701 . ?
C26 H26 0.9900 . ?
C26 C27 1.511(13) . ?
C26 C28 1.569(16) . ?
C27 H27A 0.9702 . ?
C27 H27B 0.9706 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9699 . ?
C28 H28B 0.9701 . ?
C28 H28C 0.9698 . ?

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
C4 Cu1 C5 179.1(3) . . ?
C2 O1 C1 115.9(7) . . ?
C5 N1 C6 110.8(6) . . ?
C5 N1 C20 122.6(6) . . ?
C6 N1 C20 126.6(6) . . ?
C5 N2 C7 108.5(5) . . ?
C5 N2 C8 123.9(5) . . ?
C7 N2 C8 126.9(5) . . ?
C9 C17 H17 107.5 . . ?
C9 C17 C19 109.9(7) . . ?
C19 C17 H17 107.5 . . ?
C18 C17 H17 107.5 . . ?
C18 C17 C9 114.9(7) . . ?
C18 C17 C19 109.2(11) . . ?
O1 C1 H1A 107.9 . . ?
O1 C1 H1B 109.7 . . ?
O1 C1 H1C 110.9 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 114.7(6) . . ?
O2 C2 O1 123.8(7) . . ?
O2 C2 C3 121.1(7) . . ?
C4 C3 C2 175.9(8) . . ?
C3 C4 Cu1 175.0(7) . . ?
N1 C5 Cu1 130.2(5) . . ?
N1 C5 N2 104.8(6) . . ?
N2 C5 Cu1 125.0(4) . . ?
N1 C6 H6 126.7 . . ?
C7 C6 N1 106.6(7) . . ?
C7 C6 H6 126.7 . . ?
N2 C7 H7 125.6 . . ?
C6 C7 N2 108.8(6) . . ?
C6 C7 H7 125.6 . . ?
C9 C8 N2 115.9(7) . . ?
C13 C8 N2 119.9(7) . . ?
C13 C8 C9 124.1(6) . . ?
C8 C9 C17 123.7(6) . . ?
C8 C9 C10 116.6(7) . . ?
C10 C9 C17 119.5(8) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.0(9) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(7) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 121.5 . . ?
C13 C12 C11 117.0(9) . . ?
C13 C12 H12 121.5 . . ?
C8 C13 C12 120.2(8) . . ?
C8 C13 C14 122.5(7) . . ?
C12 C13 C14 117.3(9) . . ?
C13 C14 H14 108.3 . . ?
C15 C14 C13 107.2(10) . . ?
C15 C14 H14 108.3 . . ?
C16 C14 C13 114.1(10) . . ?
C16 C14 H14 108.3 . . ?
C16 C14 C15 110.3(13) . . ?
C14 C15 H15A 110.6 . . ?
C14 C15 H15B 108.2 . . ?
C14 C15 H15C 109.6 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 108.1 . . ?
C14 C16 H16B 111.5 . . ?
C14 C16 H16C 108.8 . . ?
H16A C16 H16B 109.4 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C19 H19A 108.8 . . ?
C17 C19 H19B 107.1 . . ?
C17 C19 H19C 112.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 H18A 104.8 . . ?
C17 C18 H18B 110.6 . . ?
C17 C18 H18C 112.9 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C25 C20 N1 117.2(6) . . ?
C21 C20 N1 119.2(6) . . ?
C21 C20 C25 123.6(5) . . ?
C20 C25 C26 123.6(6) . . ?
C24 C25 C20 116.7(6) . . ?
C24 C25 C26 119.7(7) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 C25 120.2(7) . . ?
C23 C24 H24 119.9 . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.9(6) . . ?
C22 C23 H23 120.1 . . ?
C23 C22 H22 118.9 . . ?
C23 C22 C21 122.2(7) . . ?
C21 C22 H22 118.9 . . ?
C20 C21 C22 117.4(6) . . ?
C20 C21 C29 123.1(6) . . ?
C22 C21 C29 119.5(7) . . ?
C21 C29 H29 107.1 . . ?
C30 C29 C21 111.4(8) . . ?
C30 C29 H29 107.1 . . ?
C30 C29 C31 111.7(9) . . ?
C31 C29 C21 112.0(7) . . ?
C31 C29 H29 107.1 . . ?
C29 C30 H30A 108.5 . . ?
C29 C30 H30B 110.9 . . ?
C29 C30 H30C 109.0 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 108.9 . . ?
C29 C31 H31B 109.9 . . ?
C29 C31 H31C 109.7 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C25 C26 H26 109.1 . . ?
C25 C26 C27 111.4(7) . . ?
C25 C26 C28 109.3(8) . . ?
C27 C26 H26 109.1 . . ?
C27 C26 C28 108.9(11) . . ?
C28 C26 H26 109.1 . . ?
C26 C27 H27A 108.3 . . ?
C26 C27 H27B 111.1 . . ?
C26 C27 H27C 109.1 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 108.4 . . ?
C26 C28 H28C 110.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.4 . . ?

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
N1 C6 C7 N2 5.8(12) . . . . ?
N1 C20 C25 C24 -179.4(5) . . . . ?
N1 C20 C25 C26 -0.8(9) . . . . ?
N1 C20 C21 C22 -178.8(6) . . . . ?
N1 C20 C21 C29 0.1(10) . . . . ?
N2 C8 C9 C17 4.3(9) . . . . ?
N2 C8 C9 C10 179.6(5) . . . . ?
N2 C8 C13 C12 175.4(7) . . . . ?
N2 C8 C13 C14 -2.1(11) . . . . ?
C17 C9 C10 C11 179.7(7) . . . . ?
C1 O1 C2 O2 -6.9(16) . . . . ?
C1 O1 C2 C3 179.9(10) . . . . ?
C5 N1 C6 C7 -2.4(11) . . . . ?
C5 N1 C20 C25 87.8(8) . . . . ?
C5 N1 C20 C21 -95.0(8) . . . . ?
C5 N2 C7 C6 -7.1(12) . . . . ?
C5 N2 C8 C9 100.4(8) . . . . ?
C5 N2 C8 C13 -76.4(10) . . . . ?
C6 N1 C5 Cu1 179.1(6) . . . . ?
C6 N1 C5 N2 -1.9(9) . . . . ?
C6 N1 C20 C25 -89.0(9) . . . . ?
C6 N1 C20 C21 88.2(10) . . . . ?
C7 N2 C5 Cu1 -175.6(7) . . . . ?
C7 N2 C5 N1 5.3(9) . . . . ?
C7 N2 C8 C9 -90.7(11) . . . . ?
C7 N2 C8 C13 92.5(10) . . . . ?
C8 N2 C5 Cu1 -4.9(11) . . . . ?
C8 N2 C5 N1 176.1(7) . . . . ?
C8 N2 C7 C6 -177.5(9) . . . . ?
C8 C9 C10 C11 4.2(11) . . . . ?
C8 C13 C14 C15 -114.6(12) . . . . ?
C8 C13 C14 C16 122.9(11) . . . . ?
C9 C8 C13 C12 -1.1(12) . . . . ?
C9 C8 C13 C14 -178.7(7) . . . . ?
C9 C10 C11 C12 0.0(13) . . . . ?
C10 C11 C12 C13 -4.8(14) . . . . ?
C11 C12 C13 C8 5.3(13) . . . . ?
C11 C12 C13 C14 -177.0(9) . . . . ?
C12 C13 C14 C15 67.9(13) . . . . ?
C12 C13 C14 C16 -54.6(12) . . . . ?
C13 C8 C9 C17 -179.0(7) . . . . ?
C13 C8 C9 C10 -3.7(10) . . . . ?
C19 C17 C9 C8 -113.0(10) . . . . ?
C19 C17 C9 C10 71.8(10) . . . . ?
C18 C17 C9 C8 123.3(10) . . . . ?
C18 C17 C9 C10 -51.8(11) . . . . ?
C20 N1 C5 Cu1 1.8(11) . . . . ?
C20 N1 C5 N2 -179.2(7) . . . . ?
C20 N1 C6 C7 174.7(8) . . . . ?
C20 C25 C24 C23 -2.1(9) . . . . ?
C20 C25 C26 C27 -112.2(9) . . . . ?
C20 C25 C26 C28 127.5(12) . . . . ?
C20 C21 C29 C30 112.6(9) . . . . ?
C20 C21 C29 C31 -121.5(9) . . . . ?
C25 C20 C21 C22 -1.8(10) . . . . ?
C25 C20 C21 C29 177.1(6) . . . . ?
C25 C24 C23 C22 -0.8(10) . . . . ?
C24 C25 C26 C27 66.5(9) . . . . ?
C24 C25 C26 C28 -53.8(13) . . . . ?
C24 C23 C22 C21 2.6(11) . . . . ?
C23 C22 C21 C20 -1.3(10) . . . . ?
C23 C22 C21 C29 179.7(6) . . . . ?
C22 C21 C29 C30 -68.5(10) . . . . ?
C22 C21 C29 C31 57.4(10) . . . . ?
C21 C20 C25 C24 3.5(9) . . . . ?
C21 C20 C25 C26 -177.8(6) . . . . ?
C26 C25 C24 C23 179.2(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.937 0.000 434.7 33.5 ?
2 -0.500 -0.374 0.500 434.7 33.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_b_a
_database_code_depnum_ccdc_archive 'CCDC 2479571'
loop_
_audit_author_name
_audit_author_address
ABSDWE
;yanan university 
China
;
_audit_update_record             
;
2025-08-11 deposited with the CCDC.	2026-03-24 downloaded from the CCDC.
;
_audit_creation_date             2024-07-27
_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         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28
_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      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                   10.5758(9)
_cell_length_b                   19.7461(17)
_cell_length_c                   6.5522(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.700(4)
_cell_angle_gamma                90
_cell_volume                     1303.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3970
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      63.706
_cell_measurement_theta_min      6.269
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0714 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.7847.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6986
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        63.915
_diffrn_reflns_theta_max         63.915
_diffrn_reflns_theta_min         6.276
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_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                1753
_reflns_number_total             2093
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2093
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.203
_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)+(0.0922P)²+2.0170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2044
_refine_ls_wR_factor_ref         0.2185
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim N2 \\sim C7 \\sim C12 \\sim C11 \\sim C10 \\sim C9 \\sim C8:
within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A
Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C11(H11), C6(H6), C8(H8), C10(H10)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.1795(2) 0.69656(11) 0.0874(4) 0.0432(6) Uani 1 1 d . . . . .
O3 O 0.0016(2) 0.75767(11) 0.0956(4) 0.0434(6) Uani 1 1 d . . . . .
O1 O 0.5937(2) 0.71865(12) 0.1438(5) 0.0558(7) Uani 1 1 d . . . . .
N1 N 0.4005(3) 0.77136(14) 0.1135(4) 0.0401(7) Uani 1 1 d . . . . .
N2 N 0.3629(4) 0.96702(17) 0.4285(7) 0.0706(8) Uani 1 1 d . U . . .
C2 C 0.1292(3) 0.75123(16) 0.0972(5) 0.0362(7) Uani 1 1 d . . . . .
C3 C 0.1916(3) 0.81672(16) 0.1102(5) 0.0372(7) Uani 1 1 d . . . . .
H3 H 0.139810 0.855743 0.113770 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3193(3) 0.82572(15) 0.1177(5) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.3812(3) 0.89588(18) 0.1438(7) 0.0547(8) Uani 1 1 d . U . . .
C1 C -0.0729(4) 0.6955(2) 0.0732(7) 0.0555(10) Uani 1 1 d . . . . .
H1A H -0.085841 0.676671 -0.070139 0.083 Uiso 1 1 calc R U . . .
H1B H -0.159482 0.704648 0.093031 0.083 Uiso 1 1 calc R U . . .
H1C H -0.024049 0.662927 0.181344 0.083 Uiso 1 1 calc R U . . .
C13 C 0.5023(4) 0.89659(19) 0.0610(8) 0.0588(11) Uani 1 1 d . . . . .
H13A H 0.471658 0.892521 -0.097047 0.071 Uiso 1 1 calc R U . . .
H13B H 0.548619 0.940544 0.097821 0.071 Uiso 1 1 calc R U . . .
C12 C 0.2859(4) 0.95172(18) 0.0549(8) 0.0571(7) Uani 1 1 d . U . . .
C14 C 0.5987(3) 0.84007(18) 0.1536(7) 0.0558(10) Uani 1 1 d . . . . .
H14A H 0.666738 0.838806 0.078095 0.067 Uiso 1 1 calc R U . . .
H14B H 0.644407 0.849972 0.306367 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5347(3) 0.77208(18) 0.1369(6) 0.0454(8) Uani 1 1 d . . . . .
C9 C 0.1388(4) 1.0667(2) -0.0063(9) 0.0736(9) Uani 1 1 d . U . . .
H9 H 0.087388 1.107054 -0.029894 0.088 Uiso 1 1 calc R U . . .
C11 C 0.2142(4) 0.9671(2) -0.1511(8) 0.0643(8) Uani 1 1 d . U . . .
H11 H 0.215716 0.938800 -0.267534 0.077 Uiso 1 1 calc R U . . .
C6 C 0.4195(4) 0.9146(2) 0.3845(8) 0.0632(8) Uani 1 1 d . U . . .
H6 H 0.481020 0.888692 0.491920 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2081(4) 1.0514(2) 0.1965(9) 0.0736(9) Uani 1 1 d . U . . .
H8 H 0.206248 1.079930 0.312187 0.088 Uiso 1 1 calc R U . . .
C7 C 0.2829(4) 0.9920(2) 0.2310(8) 0.0651(8) Uani 1 1 d . U . . .
C10 C 0.1368(4) 1.0280(2) -0.1838(9) 0.0730(9) Uani 1 1 d . U . . .
H10 H 0.085279 1.041404 -0.323562 0.088 Uiso 1 1 calc R U . . .
H1 H 0.366(3) 0.7326(18) 0.106(5) 0.032(9) 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
O2 C2 1.214(4) . ?
O3 C2 1.352(4) . ?
O3 C1 1.442(4) . ?
O1 C15 1.220(4) . ?
N1 C4 1.380(4) . ?
N1 C15 1.380(4) . ?
N1 H1 0.84(4) . ?
N2 C6 1.272(5) . ?
N2 C7 1.403(6) . ?
C2 C3 1.443(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.348(4) . ?
C4 C5 1.520(4) . ?
C5 C13 1.534(5) . ?
C5 C12 1.488(5) . ?
C5 C6 1.549(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(5) . ?
C12 C11 1.366(6) . ?
C12 C7 1.410(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.492(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.342(7) . ?
C9 C10 1.387(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.433(6) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.393(6) . ?
C10 H10 0.9500 . ?

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
C2 O3 C1 115.7(3) . . ?
C4 N1 H1 117(2) . . ?
C15 N1 C4 127.9(3) . . ?
C15 N1 H1 115(2) . . ?
C6 N2 C7 105.7(4) . . ?
O2 C2 O3 122.4(3) . . ?
O2 C2 C3 126.9(3) . . ?
O3 C2 C3 110.7(3) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 C2 123.8(3) . . ?
C4 C3 H3 118.1 . . ?
N1 C4 C5 117.5(3) . . ?
C3 C4 N1 121.3(3) . . ?
C3 C4 C5 121.1(3) . . ?
C4 C5 C13 110.2(3) . . ?
C4 C5 C6 107.6(3) . . ?
C13 C5 C6 111.7(3) . . ?
C12 C5 C4 114.4(3) . . ?
C12 C5 C13 113.2(3) . . ?
C12 C5 C6 99.1(3) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C13 H13A 109.1 . . ?
C5 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C5 112.7(3) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C11 C12 C5 131.1(4) . . ?
C11 C12 C7 122.6(4) . . ?
C7 C12 C5 106.2(4) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.6(3) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
O1 C15 N1 119.5(3) . . ?
O1 C15 C14 124.0(3) . . ?
N1 C15 C14 116.4(3) . . ?
C8 C9 H9 117.6 . . ?
C8 C9 C10 124.7(4) . . ?
C10 C9 H9 117.6 . . ?
C12 C11 H11 121.5 . . ?
C12 C11 C10 117.0(4) . . ?
C10 C11 H11 121.5 . . ?
N2 C6 C5 115.5(4) . . ?
N2 C6 H6 122.3 . . ?
C5 C6 H6 122.3 . . ?
C9 C8 H8 121.2 . . ?
C9 C8 C7 117.6(5) . . ?
C7 C8 H8 121.2 . . ?
N2 C7 C12 113.5(4) . . ?
C8 C7 N2 126.8(4) . . ?
C8 C7 C12 119.6(5) . . ?
C9 C10 C11 118.4(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?

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 C2 C3 C4 -1.4(5) . . . . ?
O3 C2 C3 C4 179.0(3) . . . . ?
N1 C4 C5 C13 25.6(5) . . . . ?
N1 C4 C5 C12 154.6(3) . . . . ?
N1 C4 C5 C6 -96.4(3) . . . . ?
C2 C3 C4 N1 -0.1(5) . . . . ?
C2 C3 C4 C5 -176.6(3) . . . . ?
C3 C4 C5 C13 -157.8(3) . . . . ?
C3 C4 C5 C12 -28.8(5) . . . . ?
C3 C4 C5 C6 80.2(4) . . . . ?
C4 N1 C15 O1 175.0(3) . . . . ?
C4 N1 C15 C14 -4.7(5) . . . . ?
C4 C5 C13 C14 -50.8(5) . . . . ?
C4 C5 C12 C11 -66.8(5) . . . . ?
C4 C5 C12 C7 115.4(4) . . . . ?
C4 C5 C6 N2 -119.3(4) . . . . ?
C5 C13 C14 C15 49.9(5) . . . . ?
C5 C12 C11 C10 -176.0(4) . . . . ?
C5 C12 C7 N2 -2.3(4) . . . . ?
C5 C12 C7 C8 175.8(3) . . . . ?
C1 O3 C2 O2 -2.3(4) . . . . ?
C1 O3 C2 C3 177.3(3) . . . . ?
C13 C5 C12 C11 60.7(5) . . . . ?
C13 C5 C12 C7 -117.1(4) . . . . ?
C13 C5 C6 N2 119.6(4) . . . . ?
C13 C14 C15 O1 158.5(4) . . . . ?
C13 C14 C15 N1 -21.9(5) . . . . ?
C12 C5 C13 C14 179.6(3) . . . . ?
C12 C5 C6 N2 0.1(4) . . . . ?
C12 C11 C10 C9 -0.3(6) . . . . ?
C15 N1 C4 C3 -174.4(3) . . . . ?
C15 N1 C4 C5 2.2(5) . . . . ?
C9 C8 C7 N2 179.4(4) . . . . ?
C9 C8 C7 C12 1.5(6) . . . . ?
C11 C12 C7 N2 179.6(3) . . . . ?
C11 C12 C7 C8 -2.2(6) . . . . ?
C6 N2 C7 C12 2.4(5) . . . . ?
C6 N2 C7 C8 -175.7(4) . . . . ?
C6 C5 C13 C14 68.8(4) . . . . ?
C6 C5 C12 C11 179.1(4) . . . . ?
C6 C5 C12 C7 1.3(4) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C7 N2 C6 C5 -1.4(4) . . . . ?
C7 C12 C11 C10 1.5(5) . . . . ?
C10 C9 C8 C7 -0.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
