# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2023032002_0m
_database_code_depnum_ccdc_archive 'CCDC 2305021'
loop_
_audit_author_name
_audit_author_address
'shoulei wang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-11-01 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N3 O4'
_chemical_formula_weight         415.44

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8691(3)
_cell_length_b                   9.8181(3)
_cell_length_c                   12.3544(5)
_cell_angle_alpha                83.507(3)
_cell_angle_beta                 89.522(3)
_cell_angle_gamma                80.379(2)
_cell_volume                     1053.80(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.741
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13215
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.601
_diffrn_reflns_theta_max         68.479
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3854
_reflns_number_gt                2754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.1844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3854
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55519(18) 0.36672(17) 0.85715(14) 0.0600(5) Uani 1 1 d . . . . .
O2 O -0.05309(18) 0.52209(18) 0.81250(14) 0.0606(5) Uani 1 1 d . . . . .
O3 O 0.1703(2) 0.70987(18) 0.61353(14) 0.0727(5) Uani 1 1 d . . . . .
O4 O 0.2696(3) 0.83078(18) 0.72662(16) 0.0850(7) Uani 1 1 d . . . . .
N3 N 0.0206(2) 0.39323(19) 0.67149(14) 0.0490(5) Uani 1 1 d . . . . .
N2 N 0.4487(2) 0.16615(19) 0.86635(15) 0.0508(5) Uani 1 1 d . . . . .
N1 N 0.3053(2) 0.1280(2) 0.89347(16) 0.0550(5) Uani 1 1 d . . . . .
C7 C 0.4462(2) 0.3063(2) 0.86583(17) 0.0472(5) Uani 1 1 d . . . . .
C24 C 0.2781(2) 0.3962(2) 0.66663(17) 0.0441(5) Uani 1 1 d . . . . .
C13 C 0.2495(2) 0.6017(2) 0.78841(17) 0.0448(5) Uani 1 1 d . . . . .
C14 C 0.2192(2) 0.4600(2) 0.76797(16) 0.0415(5) Uani 1 1 d . . . . .
C17 C 0.0448(2) 0.4651(2) 0.75550(17) 0.0463(5) Uani 1 1 d . . . . .
C15 C 0.2256(3) 0.7169(2) 0.70019(19) 0.0502(5) Uani 1 1 d . . . . .
C19 C 0.1571(3) 0.3544(2) 0.61571(17) 0.0465(5) Uani 1 1 d . . . . .
C8 C 0.2789(2) 0.3695(2) 0.88016(17) 0.0437(5) Uani 1 1 d . . . . .
C9 C 0.2104(3) 0.2393(2) 0.90539(17) 0.0493(5) Uani 1 1 d . . . . .
C12 C 0.2708(3) 0.6102(2) 0.89329(19) 0.0530(6) Uani 1 1 d . . . . .
H12 H 0.286926 0.691165 0.920556 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2662(3) 0.4772(2) 0.96294(18) 0.0534(6) Uani 1 1 d . . . . .
H11A H 0.171003 0.480793 1.002602 0.064 Uiso 1 1 calc R U . . .
H11B H 0.351043 0.455860 1.014473 0.064 Uiso 1 1 calc R U . . .
C23 C 0.4212(3) 0.3770(3) 0.62110(19) 0.0593(6) Uani 1 1 d . . . . .
H23 H 0.502390 0.407587 0.652698 0.071 Uiso 1 1 calc R U . . .
C6 C 0.5709(3) 0.0606(2) 0.84312(19) 0.0556(6) Uani 1 1 d . . . . .
C20 C 0.1760(3) 0.2891(3) 0.5221(2) 0.0638(7) Uani 1 1 d . . . . .
H20 H 0.094545 0.260703 0.489028 0.077 Uiso 1 1 calc R U . . .
C10 C 0.0533(3) 0.2283(3) 0.9444(2) 0.0678(7) Uani 1 1 d . . . . .
H10A H -0.019414 0.267056 0.887483 0.102 Uiso 1 1 calc R U . . .
H10B H 0.032184 0.278341 1.006741 0.102 Uiso 1 1 calc R U . . .
H10C H 0.045898 0.132238 0.964329 0.102 Uiso 1 1 calc R U . . .
C5 C 0.5464(3) -0.0742(3) 0.8444(2) 0.0649(7) Uani 1 1 d . . . . .
H5 H 0.451693 -0.097159 0.864396 0.078 Uiso 1 1 calc R U . . .
C18 C -0.1302(3) 0.3745(3) 0.6373(2) 0.0683(7) Uani 1 1 d . . . . .
H18A H -0.205578 0.414445 0.686041 0.102 Uiso 1 1 calc R U . . .
H18B H -0.133238 0.276995 0.638705 0.102 Uiso 1 1 calc R U . . .
H18C H -0.151542 0.419539 0.564725 0.102 Uiso 1 1 calc R U . . .
C4 C 0.6634(4) -0.1759(3) 0.8159(2) 0.0788(9) Uani 1 1 d . . . . .
H4 H 0.646453 -0.266904 0.815986 0.095 Uiso 1 1 calc R U . . .
C21 C 0.3224(4) 0.2677(3) 0.4796(2) 0.0764(8) Uani 1 1 d . . . . .
H21 H 0.339481 0.222656 0.417236 0.092 Uiso 1 1 calc R U . . .
C22 C 0.4420(4) 0.3110(3) 0.5269(2) 0.0741(8) Uani 1 1 d . . . . .
H22 H 0.538355 0.296162 0.495885 0.089 Uiso 1 1 calc R U . . .
C1 C 0.7139(3) 0.0928(3) 0.8183(3) 0.0853(9) Uani 1 1 d . . . . .
H1 H 0.732929 0.182717 0.820470 0.102 Uiso 1 1 calc R U . . .
C16 C 0.2488(4) 0.9515(3) 0.6461(3) 0.0939(11) Uani 1 1 d . . . . .
H16A H 0.309510 0.931132 0.583408 0.141 Uiso 1 1 calc R U . . .
H16B H 0.280122 1.028217 0.676452 0.141 Uiso 1 1 calc R U . . .
H16C H 0.142899 0.975148 0.624937 0.141 Uiso 1 1 calc R U . . .
C3 C 0.8028(4) -0.1434(4) 0.7877(3) 0.0926(10) Uani 1 1 d . . . . .
H3 H 0.880275 -0.211320 0.766893 0.111 Uiso 1 1 calc R U . . .
C2 C 0.8280(4) -0.0104(4) 0.7901(3) 0.1060(12) Uani 1 1 d . . . . .
H2 H 0.924038 0.011096 0.772398 0.127 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
O1 C7 1.214(3) . ?
O2 C17 1.216(3) . ?
O3 C15 1.195(3) . ?
O4 C15 1.319(3) . ?
O4 C16 1.446(3) . ?
N3 C17 1.357(3) . ?
N3 C19 1.406(3) . ?
N3 C18 1.453(3) . ?
N2 C7 1.372(3) . ?
N2 N1 1.412(3) . ?
N2 C6 1.421(3) . ?
N1 C9 1.285(3) . ?
C7 C8 1.527(3) . ?
C24 C23 1.377(3) . ?
C24 C19 1.390(3) . ?
C24 C14 1.513(3) . ?
C13 C12 1.325(3) . ?
C13 C15 1.469(3) . ?
C13 C14 1.509(3) . ?
C14 C17 1.548(3) . ?
C14 C8 1.602(3) . ?
C19 C20 1.381(3) . ?
C8 C9 1.505(3) . ?
C8 C11 1.543(3) . ?
C9 C10 1.488(3) . ?
C12 C11 1.487(3) . ?
C12 H12 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C23 C22 1.391(4) . ?
C23 H23 0.9300 . ?
C6 C5 1.375(3) . ?
C6 C1 1.381(4) . ?
C20 C21 1.388(4) . ?
C20 H20 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C4 1.388(4) . ?
C5 H5 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 C3 1.360(5) . ?
C4 H4 0.9300 . ?
C21 C22 1.365(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C1 C2 1.379(4) . ?
C1 H1 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 C2 1.365(5) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?

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
C15 O4 C16 117.6(2) . . ?
C17 N3 C19 111.04(17) . . ?
C17 N3 C18 123.5(2) . . ?
C19 N3 C18 125.1(2) . . ?
C7 N2 N1 112.09(18) . . ?
C7 N2 C6 129.47(19) . . ?
N1 N2 C6 118.43(19) . . ?
C9 N1 N2 108.03(19) . . ?
O1 C7 N2 126.9(2) . . ?
O1 C7 C8 127.4(2) . . ?
N2 C7 C8 105.76(17) . . ?
C23 C24 C19 119.6(2) . . ?
C23 C24 C14 131.7(2) . . ?
C19 C24 C14 108.64(18) . . ?
C12 C13 C15 127.1(2) . . ?
C12 C13 C14 112.1(2) . . ?
C15 C13 C14 119.79(18) . . ?
C13 C14 C24 120.85(17) . . ?
C13 C14 C17 109.20(17) . . ?
C24 C14 C17 101.34(16) . . ?
C13 C14 C8 101.05(16) . . ?
C24 C14 C8 114.55(17) . . ?
C17 C14 C8 109.77(16) . . ?
O2 C17 N3 126.1(2) . . ?
O2 C17 C14 125.6(2) . . ?
N3 C17 C14 108.24(18) . . ?
O3 C15 O4 122.9(2) . . ?
O3 C15 C13 123.9(2) . . ?
O4 C15 C13 113.11(19) . . ?
C20 C19 C24 122.2(2) . . ?
C20 C19 N3 127.8(2) . . ?
C24 C19 N3 109.90(18) . . ?
C9 C8 C7 100.25(17) . . ?
C9 C8 C11 120.07(18) . . ?
C7 C8 C11 110.15(17) . . ?
C9 C8 C14 114.11(17) . . ?
C7 C8 C14 107.94(16) . . ?
C11 C8 C14 103.92(17) . . ?
N1 C9 C10 119.4(2) . . ?
N1 C9 C8 113.0(2) . . ?
C10 C9 C8 127.5(2) . . ?
C13 C12 C11 113.1(2) . . ?
C13 C12 H12 123.4 . . ?
C11 C12 H12 123.4 . . ?
C12 C11 C8 103.31(18) . . ?
C12 C11 H11A 111.1 . . ?
C8 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C8 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C24 C23 C22 118.7(2) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 N2 119.8(2) . . ?
C1 C6 N2 120.4(2) . . ?
C19 C20 C21 116.9(2) . . ?
C19 C20 H20 121.6 . . ?
C21 C20 H20 121.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C22 C21 C20 121.8(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?

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
C7 N2 N1 C9 2.8(3) . . . . ?
C6 N2 N1 C9 -176.59(19) . . . . ?
N1 N2 C7 O1 171.5(2) . . . . ?
C6 N2 C7 O1 -9.2(4) . . . . ?
N1 N2 C7 C8 -7.7(2) . . . . ?
C6 N2 C7 C8 171.7(2) . . . . ?
C12 C13 C14 C24 -144.7(2) . . . . ?
C15 C13 C14 C24 46.1(3) . . . . ?
C12 C13 C14 C17 98.5(2) . . . . ?
C15 C13 C14 C17 -70.6(2) . . . . ?
C12 C13 C14 C8 -17.2(2) . . . . ?
C15 C13 C14 C8 173.71(19) . . . . ?
C23 C24 C14 C13 50.9(3) . . . . ?
C19 C24 C14 C13 -128.2(2) . . . . ?
C23 C24 C14 C17 171.6(2) . . . . ?
C19 C24 C14 C17 -7.5(2) . . . . ?
C23 C24 C14 C8 -70.3(3) . . . . ?
C19 C24 C14 C8 110.6(2) . . . . ?
C19 N3 C17 O2 173.4(2) . . . . ?
C18 N3 C17 O2 0.1(4) . . . . ?
C19 N3 C17 C14 -7.6(2) . . . . ?
C18 N3 C17 C14 179.1(2) . . . . ?
C13 C14 C17 O2 -43.3(3) . . . . ?
C24 C14 C17 O2 -171.9(2) . . . . ?
C8 C14 C17 O2 66.6(3) . . . . ?
C13 C14 C17 N3 137.71(18) . . . . ?
C24 C14 C17 N3 9.1(2) . . . . ?
C8 C14 C17 N3 -112.36(19) . . . . ?
C16 O4 C15 O3 0.1(4) . . . . ?
C16 O4 C15 C13 -179.0(3) . . . . ?
C12 C13 C15 O3 -160.6(3) . . . . ?
C14 C13 C15 O3 6.7(4) . . . . ?
C12 C13 C15 O4 18.4(3) . . . . ?
C14 C13 C15 O4 -174.2(2) . . . . ?
C23 C24 C19 C20 2.4(3) . . . . ?
C14 C24 C19 C20 -178.4(2) . . . . ?
C23 C24 C19 N3 -175.61(19) . . . . ?
C14 C24 C19 N3 3.6(2) . . . . ?
C17 N3 C19 C20 -175.2(2) . . . . ?
C18 N3 C19 C20 -2.0(4) . . . . ?
C17 N3 C19 C24 2.7(3) . . . . ?
C18 N3 C19 C24 175.8(2) . . . . ?
O1 C7 C8 C9 -170.4(2) . . . . ?
N2 C7 C8 C9 8.8(2) . . . . ?
O1 C7 C8 C11 -42.9(3) . . . . ?
N2 C7 C8 C11 136.26(18) . . . . ?
O1 C7 C8 C14 70.0(3) . . . . ?
N2 C7 C8 C14 -110.90(18) . . . . ?
C13 C14 C8 C9 156.87(18) . . . . ?
C24 C14 C8 C9 -71.5(2) . . . . ?
C17 C14 C8 C9 41.6(2) . . . . ?
C13 C14 C8 C7 -92.65(18) . . . . ?
C24 C14 C8 C7 38.9(2) . . . . ?
C17 C14 C8 C7 152.12(17) . . . . ?
C13 C14 C8 C11 24.3(2) . . . . ?
C24 C14 C8 C11 155.88(17) . . . . ?
C17 C14 C8 C11 -90.9(2) . . . . ?
N2 N1 C9 C10 -174.3(2) . . . . ?
N2 N1 C9 C8 3.6(3) . . . . ?
C7 C8 C9 N1 -7.8(2) . . . . ?
C11 C8 C9 N1 -128.4(2) . . . . ?
C14 C8 C9 N1 107.3(2) . . . . ?
C7 C8 C9 C10 170.0(2) . . . . ?
C11 C8 C9 C10 49.4(3) . . . . ?
C14 C8 C9 C10 -74.9(3) . . . . ?
C15 C13 C12 C11 170.7(2) . . . . ?
C14 C13 C12 C11 2.5(3) . . . . ?
C13 C12 C11 C8 14.1(3) . . . . ?
C9 C8 C11 C12 -152.4(2) . . . . ?
C7 C8 C11 C12 92.1(2) . . . . ?
C14 C8 C11 C12 -23.3(2) . . . . ?
C19 C24 C23 C22 -2.5(4) . . . . ?
C14 C24 C23 C22 178.5(2) . . . . ?
C7 N2 C6 C5 -177.5(2) . . . . ?
N1 N2 C6 C5 1.8(3) . . . . ?
C7 N2 C6 C1 1.9(4) . . . . ?
N1 N2 C6 C1 -178.8(2) . . . . ?
C24 C19 C20 C21 -0.7(4) . . . . ?
N3 C19 C20 C21 177.0(2) . . . . ?
C1 C6 C5 C4 -3.0(4) . . . . ?
N2 C6 C5 C4 176.4(2) . . . . ?
C6 C5 C4 C3 0.7(4) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C24 C23 C22 C21 0.9(4) . . . . ?
C5 C6 C1 C2 3.0(5) . . . . ?
N2 C6 C1 C2 -176.4(3) . . . . ?
C5 C4 C3 C2 1.5(5) . . . . ?
C4 C3 C2 C1 -1.5(6) . . . . ?
C6 C1 C2 C3 -0.8(6) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_2023042001_0m
_database_code_depnum_ccdc_archive 'CCDC 2305023'
loop_
_audit_author_name
_audit_author_address
'shoulei wang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-11-01 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2901(2)
_cell_length_b                   22.9799(5)
_cell_length_c                   8.7583(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.5020(10)
_cell_angle_gamma                90
_cell_volume                     1939.86(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.751
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20558
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.847
_diffrn_reflns_theta_max         68.341
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3554
_reflns_number_gt                2767
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.4673P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.94499(16) 0.57857(7) 0.60611(19) 0.0684(4) Uani 1 1 d . . . . .
O2 O 0.42547(16) 0.65772(8) 0.5181(2) 0.0744(5) Uani 1 1 d . . . . .
N1 N 0.83129(18) 0.59521(7) 0.3346(2) 0.0578(4) Uani 1 1 d . . . . .
O4 O 1.05184(18) 0.78015(9) 1.0699(2) 0.0894(6) Uani 1 1 d . . . . .
N2 N 0.4493(2) 0.56652(9) 0.6305(2) 0.0725(6) Uani 1 1 d . . . . .
C4 C 0.64669(19) 0.65136(8) 0.3336(2) 0.0493(4) Uani 1 1 d . . . . .
C9 C 0.72142(19) 0.63140(8) 0.5040(2) 0.0499(4) Uani 1 1 d . . . . .
C10 C 0.73189(19) 0.66559(8) 0.6566(2) 0.0499(4) Uani 1 1 d . . . . .
H10 H 0.672339 0.700142 0.634419 0.060 Uiso 1 1 calc R U . . .
O3 O 1.1078(3) 0.68664(11) 1.0709(3) 0.1204(8) Uani 1 1 d . . . . .
C5 C 0.7168(2) 0.62761(8) 0.2379(2) 0.0528(5) Uani 1 1 d . . . . .
C8 C 0.8466(2) 0.59848(8) 0.4956(2) 0.0533(5) Uani 1 1 d . . . . .
C23 C 0.6852(2) 0.55294(9) 0.7192(2) 0.0583(5) Uani 1 1 d . . . . .
C11 C 0.8612(2) 0.67293(9) 0.7938(2) 0.0544(5) Uani 1 1 d . . . . .
H11 H 0.922191 0.641608 0.823223 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5345(2) 0.68719(9) 0.2615(2) 0.0590(5) Uani 1 1 d . . . . .
H3 H 0.487631 0.704246 0.323450 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4957(2) 0.61551(10) 0.5792(2) 0.0605(5) Uani 1 1 d . . . . .
C22 C 0.8055(3) 0.52338(10) 0.8049(3) 0.0684(6) Uani 1 1 d . . . . .
H22 H 0.891336 0.538253 0.811320 0.082 Uiso 1 1 calc R U . . .
C15 C 0.6512(2) 0.60861(9) 0.6252(2) 0.0519(5) Uani 1 1 d . . . . .
C12 C 0.8964(2) 0.72116(10) 0.8779(3) 0.0618(5) Uani 1 1 d . . . . .
H12 H 0.837096 0.753046 0.850224 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6748(3) 0.63718(10) 0.0723(3) 0.0676(6) Uani 1 1 d . . . . .
H6 H 0.721561 0.620348 0.009811 0.081 Uiso 1 1 calc R U . . .
C2 C 0.4924(2) 0.69751(10) 0.0947(3) 0.0676(6) Uani 1 1 d . . . . .
H2 H 0.416677 0.721617 0.045178 0.081 Uiso 1 1 calc R U . . .
C18 C 0.5584(3) 0.52983(10) 0.7162(3) 0.0695(6) Uani 1 1 d . . . . .
C13 C 1.0296(3) 0.72565(12) 1.0167(3) 0.0715(6) Uani 1 1 d . . . . .
C1 C 0.5609(3) 0.67263(11) 0.0022(3) 0.0730(6) Uani 1 1 d . . . . .
H1 H 0.530277 0.679719 -0.109375 0.088 Uiso 1 1 calc R U . . .
C7 C 0.9334(3) 0.56848(13) 0.2769(3) 0.0847(8) Uani 1 1 d . . . . .
H7A H 0.886989 0.544914 0.183032 0.127 Uiso 1 1 calc R U . . .
H7B H 0.994708 0.544571 0.361468 0.127 Uiso 1 1 calc R U . . .
H7C H 0.985917 0.598275 0.247898 0.127 Uiso 1 1 calc R U . . .
C21 C 0.7974(4) 0.47108(11) 0.8816(3) 0.0859(8) Uani 1 1 d . . . . .
H21 H 0.878370 0.450922 0.938028 0.103 Uiso 1 1 calc R U . . .
C19 C 0.5507(4) 0.47822(13) 0.7939(4) 0.0968(10) Uani 1 1 d . . . . .
H19 H 0.465657 0.463573 0.791302 0.116 Uiso 1 1 calc R U . . .
C17 C 0.3044(3) 0.55809(16) 0.6122(4) 0.1044(10) Uani 1 1 d . . . . .
H17A H 0.295791 0.557390 0.717876 0.157 Uiso 1 1 calc R U . . .
H17B H 0.272021 0.521876 0.557525 0.157 Uiso 1 1 calc R U . . .
H17C H 0.249876 0.589459 0.549298 0.157 Uiso 1 1 calc R U . . .
C20 C 0.6729(5) 0.44900(13) 0.8755(4) 0.1051(11) Uani 1 1 d . . . . .
H20 H 0.669983 0.413847 0.926833 0.126 Uiso 1 1 calc R U . . .
C14 C 1.1827(3) 0.78849(18) 1.2070(4) 0.1137(12) Uani 1 1 d . . . . .
H14A H 1.257142 0.793615 1.165976 0.171 Uiso 1 1 calc R U . . .
H14B H 1.200873 0.754952 1.276661 0.171 Uiso 1 1 calc R U . . .
H14C H 1.175679 0.822345 1.267802 0.171 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
O1 C8 1.218(2) . ?
O2 C16 1.216(3) . ?
N1 C8 1.365(3) . ?
N1 C5 1.400(3) . ?
N1 C7 1.452(3) . ?
O4 C13 1.328(3) . ?
O4 C14 1.469(3) . ?
N2 C16 1.359(3) . ?
N2 C18 1.395(3) . ?
N2 C17 1.455(3) . ?
C4 C3 1.378(3) . ?
C4 C5 1.394(3) . ?
C4 C9 1.492(3) . ?
C9 C8 1.518(3) . ?
C9 C10 1.521(2) . ?
C9 C15 1.568(2) . ?
C10 C11 1.457(3) . ?
C10 C15 1.523(3) . ?
C10 H10 0.9800 . ?
O3 C13 1.187(3) . ?
C5 C6 1.379(3) . ?
C23 C22 1.380(3) . ?
C23 C18 1.401(3) . ?
C23 C15 1.495(3) . ?
C11 C12 1.310(3) . ?
C11 H11 0.9300 . ?
C3 C2 1.391(3) . ?
C3 H3 0.9300 . ?
C16 C15 1.515(3) . ?
C22 C21 1.394(3) . ?
C22 H22 0.9300 . ?
C12 C13 1.483(3) . ?
C12 H12 0.9300 . ?
C6 C1 1.382(3) . ?
C6 H6 0.9300 . ?
C2 C1 1.371(3) . ?
C2 H2 0.9300 . ?
C18 C19 1.383(4) . ?
C1 H1 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C21 C20 1.361(5) . ?
C21 H21 0.9300 . ?
C19 C20 1.384(5) . ?
C19 H19 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C8 N1 C5 111.34(15) . . ?
C8 N1 C7 123.18(19) . . ?
C5 N1 C7 124.90(18) . . ?
C13 O4 C14 113.9(2) . . ?
C16 N2 C18 111.62(19) . . ?
C16 N2 C17 122.6(2) . . ?
C18 N2 C17 125.4(2) . . ?
C3 C4 C5 119.00(18) . . ?
C3 C4 C9 134.27(17) . . ?
C5 C4 C9 106.69(16) . . ?
C4 C9 C8 104.68(15) . . ?
C4 C9 C10 124.98(16) . . ?
C8 C9 C10 120.00(16) . . ?
C4 C9 C15 125.54(16) . . ?
C8 C9 C15 117.82(16) . . ?
C10 C9 C15 59.05(12) . . ?
C11 C10 C9 123.18(16) . . ?
C11 C10 C15 122.11(17) . . ?
C9 C10 C15 62.02(12) . . ?
C11 C10 H10 113.4 . . ?
C9 C10 H10 113.4 . . ?
C15 C10 H10 113.4 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 N1 127.48(18) . . ?
C4 C5 N1 110.33(16) . . ?
O1 C8 N1 124.27(18) . . ?
O1 C8 C9 129.18(18) . . ?
N1 C8 C9 106.54(16) . . ?
C22 C23 C18 118.4(2) . . ?
C22 C23 C15 135.5(2) . . ?
C18 C23 C15 106.1(2) . . ?
C12 C11 C10 123.7(2) . . ?
C12 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C4 C3 C2 119.12(19) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
O2 C16 N2 125.6(2) . . ?
O2 C16 C15 127.6(2) . . ?
N2 C16 C15 106.6(2) . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C23 C15 C16 104.96(17) . . ?
C23 C15 C10 128.90(17) . . ?
C16 C15 C10 114.60(17) . . ?
C23 C15 C9 125.69(16) . . ?
C16 C15 C9 118.65(17) . . ?
C10 C15 C9 58.93(12) . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C5 C6 C1 117.8(2) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
C1 C2 C3 120.9(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C19 C18 N2 127.5(3) . . ?
C19 C18 C23 122.0(3) . . ?
N2 C18 C23 110.5(2) . . ?
O3 C13 O4 124.2(2) . . ?
O3 C13 C12 125.3(2) . . ?
O4 C13 C12 110.4(2) . . ?
C2 C1 C6 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C18 C19 C20 118.1(3) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C3 C4 C9 C8 -173.0(2) . . . . ?
C5 C4 C9 C8 4.56(19) . . . . ?
C3 C4 C9 C10 -28.5(3) . . . . ?
C5 C4 C9 C10 149.06(18) . . . . ?
C3 C4 C9 C15 45.8(3) . . . . ?
C5 C4 C9 C15 -136.69(18) . . . . ?
C4 C9 C10 C11 -134.1(2) . . . . ?
C8 C9 C10 C11 5.4(3) . . . . ?
C15 C9 C10 C11 111.8(2) . . . . ?
C4 C9 C10 C15 114.1(2) . . . . ?
C8 C9 C10 C15 -106.39(19) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C9 C4 C5 C6 179.75(19) . . . . ?
C3 C4 C5 N1 176.86(17) . . . . ?
C9 C4 C5 N1 -1.1(2) . . . . ?
C8 N1 C5 C6 175.8(2) . . . . ?
C7 N1 C5 C6 4.3(3) . . . . ?
C8 N1 C5 C4 -3.3(2) . . . . ?
C7 N1 C5 C4 -174.8(2) . . . . ?
C5 N1 C8 O1 -173.13(19) . . . . ?
C7 N1 C8 O1 -1.5(3) . . . . ?
C5 N1 C8 C9 6.1(2) . . . . ?
C7 N1 C8 C9 177.8(2) . . . . ?
C4 C9 C8 O1 172.7(2) . . . . ?
C10 C9 C8 O1 26.0(3) . . . . ?
C15 C9 C8 O1 -42.4(3) . . . . ?
C4 C9 C8 N1 -6.5(2) . . . . ?
C10 C9 C8 N1 -153.15(17) . . . . ?
C15 C9 C8 N1 138.37(17) . . . . ?
C9 C10 C11 C12 141.9(2) . . . . ?
C15 C10 C11 C12 -142.6(2) . . . . ?
C5 C4 C3 C2 1.6(3) . . . . ?
C9 C4 C3 C2 178.9(2) . . . . ?
C18 N2 C16 O2 -171.3(2) . . . . ?
C17 N2 C16 O2 2.2(4) . . . . ?
C18 N2 C16 C15 4.5(2) . . . . ?
C17 N2 C16 C15 177.9(2) . . . . ?
C18 C23 C22 C21 1.7(3) . . . . ?
C15 C23 C22 C21 179.1(2) . . . . ?
C22 C23 C15 C16 -174.4(2) . . . . ?
C18 C23 C15 C16 3.2(2) . . . . ?
C22 C23 C15 C10 -34.1(3) . . . . ?
C18 C23 C15 C10 143.48(19) . . . . ?
C22 C23 C15 C9 42.2(3) . . . . ?
C18 C23 C15 C9 -140.23(19) . . . . ?
O2 C16 C15 C23 171.0(2) . . . . ?
N2 C16 C15 C23 -4.7(2) . . . . ?
O2 C16 C15 C10 24.2(3) . . . . ?
N2 C16 C15 C10 -151.51(16) . . . . ?
O2 C16 C15 C9 -42.5(3) . . . . ?
N2 C16 C15 C9 141.86(17) . . . . ?
C11 C10 C15 C23 -0.6(3) . . . . ?
C9 C10 C15 C23 112.9(2) . . . . ?
C11 C10 C15 C16 136.67(18) . . . . ?
C9 C10 C15 C16 -109.86(18) . . . . ?
C11 C10 C15 C9 -113.47(19) . . . . ?
C4 C9 C15 C23 128.8(2) . . . . ?
C8 C9 C15 C23 -8.0(3) . . . . ?
C10 C9 C15 C23 -118.0(2) . . . . ?
C4 C9 C15 C16 -10.2(3) . . . . ?
C8 C9 C15 C16 -146.98(18) . . . . ?
C10 C9 C15 C16 102.98(19) . . . . ?
C4 C9 C15 C10 -113.2(2) . . . . ?
C8 C9 C15 C10 110.04(19) . . . . ?
C10 C11 C12 C13 179.77(19) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
N1 C5 C6 C1 -177.6(2) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C16 N2 C18 C19 175.9(2) . . . . ?
C17 N2 C18 C19 2.7(4) . . . . ?
C16 N2 C18 C23 -2.5(2) . . . . ?
C17 N2 C18 C23 -175.7(2) . . . . ?
C22 C23 C18 C19 -1.1(3) . . . . ?
C15 C23 C18 C19 -179.2(2) . . . . ?
C22 C23 C18 N2 177.42(18) . . . . ?
C15 C23 C18 N2 -0.7(2) . . . . ?
C14 O4 C13 O3 -1.3(4) . . . . ?
C14 O4 C13 C12 -179.5(2) . . . . ?
C11 C12 C13 O3 -6.3(4) . . . . ?
C11 C12 C13 O4 171.8(2) . . . . ?
C3 C2 C1 C6 -0.8(4) . . . . ?
C5 C6 C1 C2 0.2(4) . . . . ?
C23 C22 C21 C20 -0.9(4) . . . . ?
N2 C18 C19 C20 -178.6(2) . . . . ?
C23 C18 C19 C20 -0.4(4) . . . . ?
C22 C21 C20 C19 -0.6(4) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.033

