# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_cu_20230517zyw_0m
_database_code_depnum_ccdc_archive 'CCDC 2395526'
loop_
_audit_author_name
_audit_author_address
'Xiaodi Yang'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-03 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 Cl N2 O4'
_chemical_formula_weight         436.88

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.5837(3)
_cell_length_b                   6.1999(2)
_cell_length_c                   13.8988(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.4440(10)
_cell_angle_gamma                90
_cell_volume                     1077.50(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    306(2)
_cell_measurement_reflns_used    8091
_cell_measurement_theta_min      3.1999
_cell_measurement_theta_max      64.9893

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.851
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      306(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16093
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.200
_diffrn_reflns_theta_max         65.132
_diffrn_reflns_theta_full        65.132
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3666
_reflns_number_gt                3186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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)+(0.0323P)²+0.1685P] 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_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl1 Cl 0.71797(9) 0.4580(4) 0.13008(11) 0.1496(8) Uani 1 1 d . . . . .
O1 O 0.0963(3) 0.8635(5) 0.1003(2) 0.1062(11) Uani 1 1 d . . . . .
O2 O 0.0371(2) 0.6535(5) 0.49196(19) 0.0769(7) Uani 1 1 d . . . . .
O3 O 0.21721(18) 0.1333(4) 0.41149(16) 0.0646(6) Uani 1 1 d . . . . .
O4 O 0.0995(2) 0.5347(5) 0.63869(17) 0.0797(8) Uani 1 1 d . . . . .
N1 N 0.21055(18) 0.3943(4) 0.21103(17) 0.0500(6) Uani 1 1 d . . . . .
N3 N 0.16400(17) 0.3818(4) 0.51265(16) 0.0470(6) Uani 1 1 d . . . . .
C1 C 0.5802(3) 0.4206(9) 0.1254(3) 0.0809(13) Uani 1 1 d . . . . .
C2D C 0.1032(2) 0.4117(5) 0.3361(2) 0.0450(6) Uani 1 1 d . . . . .
H2D H 0.027802 0.421927 0.347087 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5126(3) 0.5746(8) 0.0846(3) 0.0816(13) Uani 1 1 d . . . . .
H2 H 0.539173 0.700125 0.059560 0.098 Uiso 1 1 calc R U . . .
C3 C 0.4040(3) 0.5414(6) 0.0811(2) 0.0648(9) Uani 1 1 d . . . . .
H20 H 0.357379 0.646059 0.053190 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3626(2) 0.3564(5) 0.1181(2) 0.0535(7) Uani 1 1 d . . . . .
C5 C 0.2441(3) 0.3223(6) 0.1180(2) 0.0622(9) Uani 1 1 d . . . . .
H17 H 0.205733 0.403223 0.065341 0.075 Uiso 1 1 calc R U . . .
H3 H 0.227272 0.170673 0.108116 0.075 Uiso 1 1 calc R U . . .
C6 C 0.1130(2) 0.2943(5) 0.2398(2) 0.0507(7) Uani 1 1 d . . . . .
H5 H 0.121926 0.138478 0.249320 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1653(2) 0.2965(5) 0.4194(2) 0.0460(6) Uani 1 1 d . . . . .
C8 C 0.2215(2) 0.2695(6) 0.5954(2) 0.0559(8) Uani 1 1 d . . . . .
H13 H 0.206645 0.114497 0.590424 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3410(2) 0.3076(5) 0.6043(2) 0.0466(7) Uani 1 1 d . . . . .
C10 C 0.4094(2) 0.1469(6) 0.6416(2) 0.0556(7) Uani 1 1 d . . . . .
H12 H 0.381636 0.014669 0.658225 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5193(3) 0.1804(6) 0.6547(2) 0.0614(9) Uani 1 1 d . . . . .
H9 H 0.564755 0.071823 0.680761 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5603(2) 0.3745(6) 0.6290(2) 0.0576(8) Uani 1 1 d . . . . .
H1 H 0.633845 0.397088 0.637503 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1863(2) 0.6233(5) 0.2172(2) 0.0532(7) Uani 1 1 d . . . . .
H16 H 0.250226 0.711443 0.212973 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1478(2) 0.6401(5) 0.3182(2) 0.0509(7) Uani 1 1 d . . . . .
H15 H 0.092482 0.748772 0.319073 0.061 Uiso 1 1 calc R U . . .
H4 H 0.206627 0.675904 0.366827 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0167(3) 0.3453(6) 0.1690(2) 0.0628(9) Uani 1 1 d . . . . .
H6 H -0.038893 0.246260 0.158848 0.075 Uiso 1 1 calc R U . . .
C16 C 0.0108(3) 0.5311(7) 0.1210(3) 0.0685(9) Uani 1 1 d . . . . .
H7 H -0.047433 0.559885 0.075466 0.082 Uiso 1 1 calc R U . . .
C17 C 0.0960(3) 0.6891(6) 0.1402(3) 0.0676(9) Uani 1 1 d . . . . .
C18 C 0.0940(3) 0.5340(6) 0.5409(2) 0.0572(8) Uani 1 1 d . . . . .
C19 C 0.1672(3) 0.3661(8) 0.6789(3) 0.0811(13) Uani 1 1 d . . . . .
H14 H 0.125550 0.256862 0.707777 0.097 Uiso 1 1 calc R U . . .
H8 H 0.220287 0.422545 0.728440 0.097 Uiso 1 1 calc R U . . .
C20 C 0.4935(2) 0.5353(6) 0.5907(2) 0.0568(8) Uani 1 1 d . . . . .
H11 H 0.521605 0.666220 0.572875 0.068 Uiso 1 1 calc R U . . .
C21 C 0.3836(2) 0.5016(6) 0.5789(2) 0.0554(8) Uani 1 1 d . . . . .
H10 H 0.338265 0.611073 0.553504 0.066 Uiso 1 1 calc R U . . .
C22 C 0.4339(3) 0.2027(7) 0.1593(2) 0.0686(9) Uani 1 1 d . . . . .
H18 H 0.407876 0.077176 0.184914 0.082 Uiso 1 1 calc R U . . .
C23 C 0.5424(3) 0.2338(8) 0.1628(3) 0.0839(13) Uani 1 1 d . . . . .
H19 H 0.589782 0.129711 0.190118 0.101 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
Cl1 C1 1.743(4) . ?
O1 C17 1.215(5) . ?
O2 C18 1.189(4) . ?
O3 C7 1.215(4) . ?
O4 C18 1.354(4) . ?
O4 C19 1.422(5) . ?
N1 C13 1.457(4) . ?
N1 C6 1.469(4) . ?
N1 C5 1.474(4) . ?
N3 C18 1.377(4) . ?
N3 C7 1.402(4) . ?
N3 C8 1.464(4) . ?
C1 C2 1.360(6) . ?
C1 C23 1.375(7) . ?
C2D C7 1.503(4) . ?
C2D C6 1.541(4) . ?
C2D C14 1.554(4) . ?
C2D H2D 0.9800 . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H20 0.9300 . ?
C4 C22 1.388(5) . ?
C4 C5 1.506(4) . ?
C5 H17 0.9700 . ?
C5 H3 0.9700 . ?
C6 C15 1.506(4) . ?
C6 H5 0.9800 . ?
C8 C9 1.514(4) . ?
C8 C19 1.533(5) . ?
C8 H13 0.9800 . ?
C9 C21 1.379(5) . ?
C9 C10 1.379(4) . ?
C10 C11 1.390(4) . ?
C10 H12 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H9 0.9300 . ?
C12 C20 1.373(5) . ?
C12 H1 0.9300 . ?
C13 C17 1.526(5) . ?
C13 C14 1.539(4) . ?
C13 H16 0.9800 . ?
C14 H15 0.9700 . ?
C14 H4 0.9700 . ?
C15 C16 1.329(5) . ?
C15 H6 0.9300 . ?
C16 C17 1.455(5) . ?
C16 H7 0.9300 . ?
C19 H14 0.9700 . ?
C19 H8 0.9700 . ?
C20 C21 1.390(4) . ?
C20 H11 0.9300 . ?
C21 H10 0.9300 . ?
C22 C23 1.375(5) . ?
C22 H18 0.9300 . ?
C23 H19 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
C18 O4 C19 110.7(3) . . ?
C13 N1 C6 102.0(2) . . ?
C13 N1 C5 115.4(3) . . ?
C6 N1 C5 116.2(2) . . ?
C18 N3 C7 126.6(3) . . ?
C18 N3 C8 112.2(2) . . ?
C7 N3 C8 119.4(3) . . ?
C2 C1 C23 121.5(3) . . ?
C2 C1 Cl1 119.7(4) . . ?
C23 C1 Cl1 118.8(4) . . ?
C7 C2D C6 111.1(2) . . ?
C7 C2D C14 113.0(2) . . ?
C6 C2D C14 103.0(2) . . ?
C7 C2D H2D 109.9 . . ?
C6 C2D H2D 109.9 . . ?
C14 C2D H2D 109.9 . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H20 119.2 . . ?
C4 C3 H20 119.2 . . ?
C3 C4 C22 118.1(3) . . ?
C3 C4 C5 122.1(3) . . ?
C22 C4 C5 119.8(3) . . ?
N1 C5 C4 109.8(2) . . ?
N1 C5 H17 109.7 . . ?
C4 C5 H17 109.7 . . ?
N1 C5 H3 109.7 . . ?
C4 C5 H3 109.7 . . ?
H17 C5 H3 108.2 . . ?
N1 C6 C15 111.7(3) . . ?
N1 C6 C2D 100.8(2) . . ?
C15 C6 C2D 109.3(2) . . ?
N1 C6 H5 111.5 . . ?
C15 C6 H5 111.5 . . ?
C2D C6 H5 111.5 . . ?
O3 C7 N3 117.4(3) . . ?
O3 C7 C2D 124.3(3) . . ?
N3 C7 C2D 118.3(2) . . ?
N3 C8 C9 112.9(2) . . ?
N3 C8 C19 100.7(3) . . ?
C9 C8 C19 113.6(3) . . ?
N3 C8 H13 109.8 . . ?
C9 C8 H13 109.8 . . ?
C19 C8 H13 109.8 . . ?
C21 C9 C10 118.9(3) . . ?
C21 C9 C8 121.7(3) . . ?
C10 C9 C8 119.4(3) . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H12 119.6 . . ?
C11 C10 H12 119.6 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H9 120.2 . . ?
C10 C11 H9 120.2 . . ?
C20 C12 C11 120.4(3) . . ?
C20 C12 H1 119.8 . . ?
C11 C12 H1 119.8 . . ?
N1 C13 C17 111.3(3) . . ?
N1 C13 C14 102.1(3) . . ?
C17 C13 C14 109.7(3) . . ?
N1 C13 H16 111.1 . . ?
C17 C13 H16 111.1 . . ?
C14 C13 H16 111.1 . . ?
C13 C14 C2D 103.9(2) . . ?
C13 C14 H15 111.0 . . ?
C2D C14 H15 111.0 . . ?
C13 C14 H4 111.0 . . ?
C2D C14 H4 111.0 . . ?
H15 C14 H4 109.0 . . ?
C16 C15 C6 120.4(3) . . ?
C16 C15 H6 119.8 . . ?
C6 C15 H6 119.8 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H7 120.2 . . ?
C17 C16 H7 120.2 . . ?
O1 C17 C16 123.7(4) . . ?
O1 C17 C13 121.2(3) . . ?
C16 C17 C13 115.1(3) . . ?
O2 C18 O4 122.1(3) . . ?
O2 C18 N3 128.8(3) . . ?
O4 C18 N3 109.0(3) . . ?
O4 C19 C8 106.7(3) . . ?
O4 C19 H14 110.4 . . ?
C8 C19 H14 110.4 . . ?
O4 C19 H8 110.4 . . ?
C8 C19 H8 110.4 . . ?
H14 C19 H8 108.6 . . ?
C12 C20 C21 119.7(3) . . ?
C12 C20 H11 120.2 . . ?
C21 C20 H11 120.2 . . ?
C9 C21 C20 120.7(3) . . ?
C9 C21 H10 119.6 . . ?
C20 C21 H10 119.6 . . ?
C23 C22 C4 120.7(4) . . ?
C23 C22 H18 119.6 . . ?
C4 C22 H18 119.6 . . ?
C22 C23 C1 119.3(4) . . ?
C22 C23 H19 120.4 . . ?
C1 C23 H19 120.4 . . ?

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
C23 C1 C2 C3 0.1(6) . . . . ?
Cl1 C1 C2 C3 179.6(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C22 0.0(5) . . . . ?
C2 C3 C4 C5 177.6(3) . . . . ?
C13 N1 C5 C4 85.4(3) . . . . ?
C6 N1 C5 C4 -155.2(3) . . . . ?
C3 C4 C5 N1 -93.8(4) . . . . ?
C22 C4 C5 N1 83.9(4) . . . . ?
C13 N1 C6 C15 63.8(3) . . . . ?
C5 N1 C6 C15 -62.6(4) . . . . ?
C13 N1 C6 C2D -52.3(3) . . . . ?
C5 N1 C6 C2D -178.7(3) . . . . ?
C7 C2D C6 N1 -87.8(3) . . . . ?
C14 C2D C6 N1 33.5(3) . . . . ?
C7 C2D C6 C15 154.5(3) . . . . ?
C14 C2D C6 C15 -84.3(3) . . . . ?
C18 N3 C7 O3 -165.0(3) . . . . ?
C8 N3 C7 O3 -1.7(4) . . . . ?
C18 N3 C7 C2D 15.1(4) . . . . ?
C8 N3 C7 C2D 178.4(2) . . . . ?
C6 C2D C7 O3 0.6(4) . . . . ?
C14 C2D C7 O3 -114.6(3) . . . . ?
C6 C2D C7 N3 -179.5(2) . . . . ?
C14 C2D C7 N3 65.3(3) . . . . ?
C18 N3 C8 C9 -116.8(3) . . . . ?
C7 N3 C8 C9 77.7(3) . . . . ?
C18 N3 C8 C19 4.7(4) . . . . ?
C7 N3 C8 C19 -160.8(3) . . . . ?
N3 C8 C9 C21 34.1(4) . . . . ?
C19 C8 C9 C21 -79.8(4) . . . . ?
N3 C8 C9 C10 -148.0(3) . . . . ?
C19 C8 C9 C10 98.1(4) . . . . ?
C21 C9 C10 C11 0.8(5) . . . . ?
C8 C9 C10 C11 -177.1(3) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C11 C12 C20 0.2(5) . . . . ?
C6 N1 C13 C17 -67.3(3) . . . . ?
C5 N1 C13 C17 59.5(3) . . . . ?
C6 N1 C13 C14 49.6(3) . . . . ?
C5 N1 C13 C14 176.5(2) . . . . ?
N1 C13 C14 C2D -26.8(3) . . . . ?
C17 C13 C14 C2D 91.3(3) . . . . ?
C7 C2D C14 C13 115.7(3) . . . . ?
C6 C2D C14 C13 -4.2(3) . . . . ?
N1 C6 C15 C16 -31.0(4) . . . . ?
C2D C6 C15 C16 79.7(4) . . . . ?
C6 C15 C16 C17 -2.5(5) . . . . ?
C15 C16 C17 O1 -179.2(4) . . . . ?
C15 C16 C17 C13 -0.6(5) . . . . ?
N1 C13 C17 O1 -143.5(4) . . . . ?
C14 C13 C17 O1 104.3(4) . . . . ?
N1 C13 C17 C16 37.9(4) . . . . ?
C14 C13 C17 C16 -74.3(4) . . . . ?
C19 O4 C18 O2 175.7(4) . . . . ?
C19 O4 C18 N3 -5.5(4) . . . . ?
C7 N3 C18 O2 -17.0(6) . . . . ?
C8 N3 C18 O2 178.8(4) . . . . ?
C7 N3 C18 O4 164.4(3) . . . . ?
C8 N3 C18 O4 0.1(4) . . . . ?
C18 O4 C19 C8 8.4(4) . . . . ?
N3 C8 C19 O4 -7.6(4) . . . . ?
C9 C8 C19 O4 113.4(3) . . . . ?
C11 C12 C20 C21 0.5(5) . . . . ?
C10 C9 C21 C20 -0.1(5) . . . . ?
C8 C9 C21 C20 177.8(3) . . . . ?
C12 C20 C21 C9 -0.6(5) . . . . ?
C3 C4 C22 C23 -0.3(5) . . . . ?
C5 C4 C22 C23 -178.0(3) . . . . ?
C4 C22 C23 C1 0.5(5) . . . . ?
C2 C1 C23 C22 -0.4(6) . . . . ?
Cl1 C1 C23 C22 -179.9(3) . . . . ?

_refine_diff_density_max         0.109
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_cu_20231107_ZYW_1X_28_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2402960'
loop_
_audit_author_name
_audit_author_address
'Xiaodi Yang'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2024-11-15 deposited with the CCDC.	2025-02-03 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            'C30 H25 Cl N2 O4'
_chemical_formula_weight         512.97

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.6891(4)
_cell_length_b                   8.3323(3)
_cell_length_c                   13.3055(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.156(2)
_cell_angle_gamma                90
_cell_volume                     1311.97(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    8529
_cell_measurement_theta_min      3.5619
_cell_measurement_theta_max      63.4421

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.603
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.772
_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  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23724
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.562
_diffrn_reflns_theta_max         65.253
_diffrn_reflns_theta_full        65.253
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4440
_reflns_number_gt                3233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

_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)+(0.0770P)²+0.1578P] 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_abs_structure_details 
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.104(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4440
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Cl1 Cl 0.6815(2) 0.2999(5) 0.7855(3) 0.2073(18) Uani 1 1 d . . . . .
O1 O 0.1016(6) 0.1458(9) 1.0962(6) 0.175(3) Uani 1 1 d . . . . .
O2 O 0.1841(3) 0.8580(4) 0.6946(3) 0.0818(9) Uani 1 1 d . . . . .
O3 O 0.1667(3) 0.7682(4) 0.8453(3) 0.0916(10) Uani 1 1 d . . . . .
O4 O -0.0096(3) 0.4093(4) 0.6401(3) 0.0876(10) Uani 1 1 d . . . . .
N1 N 0.1966(4) 0.2470(5) 0.8831(4) 0.0957(13) Uani 1 1 d . . . . .
N3 N 0.1159(3) 0.6111(4) 0.6895(3) 0.0709(9) Uani 1 1 d . . . . .
C1 C 0.5673(5) 0.2584(10) 0.8238(7) 0.119(2) Uani 1 1 d . . . . .
C2A C 0.0728(4) 0.4586(6) 0.8304(4) 0.0765(12) Uani 1 1 d . . . . .
H2A H 0.049045 0.553629 0.860165 0.092 Uiso 1 1 calc R U . . .
C2 C 0.4790(7) 0.1715(12) 0.7602(7) 0.135(3) Uani 1 1 d . . . . .
H2 H 0.476910 0.130138 0.694608 0.162 Uiso 1 1 calc R U . . .
C3 C 0.3902(7) 0.1462(9) 0.7978(7) 0.122(2) Uani 1 1 d . . . . .
H3 H 0.327379 0.088996 0.754261 0.147 Uiso 1 1 calc R U . . .
C4A C 0.1294(4) 0.5083(6) 0.5159(4) 0.0701(10) Uani 1 1 d . . . . .
C4 C 0.3911(6) 0.2003(6) 0.8937(6) 0.0996(18) Uani 1 1 d . . . . .
C5 C 0.2969(7) 0.1583(9) 0.9341(7) 0.129(3) Uani 1 1 d . . . . .
H6 H 0.280036 0.044754 0.922379 0.154 Uiso 1 1 calc R U . . .
H7 H 0.322952 0.177724 1.011151 0.154 Uiso 1 1 calc R U . . .
C6 C 0.1981(4) 0.4212(6) 0.8971(4) 0.0765(12) Uani 1 1 d . . . . .
H22 H 0.249047 0.473378 0.866613 0.092 Uiso 1 1 calc R U . . .
C7 C 0.0537(4) 0.4868(5) 0.7133(4) 0.0724(11) Uani 1 1 d . . . . .
C8 C 0.1027(4) 0.6439(5) 0.5763(4) 0.0711(11) Uani 1 1 d . . . . .
H14 H 0.024734 0.678403 0.537178 0.085 Uiso 1 1 calc R U . . .
C9 C 0.1816(4) 0.7921(5) 0.5929(4) 0.0772(12) Uani 1 1 d . . . . .
H19 H 0.146248 0.870086 0.535417 0.093 Uiso 1 1 calc R U . . .
C10 C 0.3001(4) 0.7620(6) 0.5999(4) 0.0812(12) Uani 1 1 d . . . . .
C11 C 0.3298(7) 0.7980(10) 0.5140(7) 0.125(2) Uani 1 1 d . . . . .
H18 H 0.276075 0.837498 0.450883 0.151 Uiso 1 1 calc R U . . .
C12 C 0.4420(11) 0.7754(18) 0.5210(11) 0.177(4) Uani 1 1 d . . . . .
H17 H 0.462339 0.799789 0.462227 0.212 Uiso 1 1 calc R U . . .
C13 C 0.5208(9) 0.7179(17) 0.6130(12) 0.174(4) Uani 1 1 d . . . . .
H1 H 0.594657 0.702705 0.616650 0.209 Uiso 1 1 calc R U . . .
C14 C 0.4817(8) 0.2847(10) 0.9522(7) 0.139(3) Uani 1 1 d . . . . .
H4 H 0.484941 0.326275 1.018156 0.167 Uiso 1 1 calc R U . . .
C15 C 0.5704(7) 0.3124(11) 0.9184(10) 0.150(3) Uani 1 1 d . . . . .
H5 H 0.633057 0.369545 0.962310 0.180 Uiso 1 1 calc R U . . .
C16 C 0.1044(7) 0.1997(7) 0.9192(6) 0.109(2) Uani 1 1 d . . . . .
H24 H 0.083737 0.086881 0.902282 0.131 Uiso 1 1 calc R U . . .
C17 C 0.1328(8) 0.2336(11) 1.0386(7) 0.130(3) Uani 1 1 d . . . . .
C18 C 0.1915(8) 0.3823(11) 1.0778(6) 0.132(3) Uani 1 1 d . . . . .
H23 H 0.208500 0.413164 1.149065 0.158 Uiso 1 1 calc R U . . .
C19 C 0.2212(6) 0.4748(8) 1.0111(5) 0.1064(19) Uani 1 1 d . . . . .
H8 H 0.256293 0.572926 1.034829 0.128 Uiso 1 1 calc R U . . .
C20 C 0.1570(4) 0.7468(6) 0.7533(4) 0.0758(12) Uani 1 1 d . . . . .
C21 C 0.2046(4) 0.3848(6) 0.5642(4) 0.0823(13) Uani 1 1 d . . . . .
H9 H 0.239737 0.381674 0.638816 0.099 Uiso 1 1 calc R U . . .
C22 C 0.2272(5) 0.2671(7) 0.5020(5) 0.0961(15) Uani 1 1 d . . . . .
H13 H 0.277856 0.185439 0.534980 0.115 Uiso 1 1 calc R U . . .
C23 C 0.1759(5) 0.2693(8) 0.3922(5) 0.0936(15) Uani 1 1 d . . . . .
H12 H 0.191938 0.189710 0.350834 0.112 Uiso 1 1 calc R U . . .
C24 C 0.1014(5) 0.3882(7) 0.3436(4) 0.0885(14) Uani 1 1 d . . . . .
H10 H 0.066951 0.389747 0.268923 0.106 Uiso 1 1 calc R U . . .
C25 C 0.0766(5) 0.5060(7) 0.4038(4) 0.0822(13) Uani 1 1 d . . . . .
H11 H 0.024039 0.584920 0.369658 0.099 Uiso 1 1 calc R U . . .
C26 C 0.4929(6) 0.6829(11) 0.6991(9) 0.136(3) Uani 1 1 d . . . . .
H16 H 0.547011 0.644277 0.762260 0.163 Uiso 1 1 calc R U . . .
C27 C 0.3821(5) 0.7055(8) 0.6917(6) 0.1049(19) Uani 1 1 d . . . . .
H15 H 0.362719 0.681488 0.751059 0.126 Uiso 1 1 calc R U . . .
C28 C 0.0118(6) 0.3107(7) 0.8502(5) 0.1003(18) Uani 1 1 d . . . . .
H21 H -0.038462 0.340031 0.887465 0.120 Uiso 1 1 calc R U . . .
H20 H -0.032056 0.259425 0.782575 0.120 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
Cl1 C1 1.736(8) . ?
O1 C17 1.224(8) . ?
O2 C20 1.334(6) . ?
O2 C9 1.451(6) . ?
O3 C20 1.197(6) . ?
O4 C7 1.203(6) . ?
N1 C5 1.416(9) . ?
N1 C6 1.462(7) . ?
N1 C16 1.470(7) . ?
N3 C20 1.397(6) . ?
N3 C7 1.406(6) . ?
N3 C8 1.479(6) . ?
C1 C15 1.324(13) . ?
C1 C2 1.346(12) . ?
C2A C7 1.507(7) . ?
C2A C28 1.527(7) . ?
C2A C6 1.548(7) . ?
C2A H2A 0.9800 . ?
C2 C3 1.404(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(10) . ?
C3 H3 0.9300 . ?
C4A C21 1.393(7) . ?
C4A C25 1.398(7) . ?
C4A C8 1.495(7) . ?
C4 C14 1.332(10) . ?
C4 C5 1.518(10) . ?
C5 H6 0.9700 . ?
C5 H7 0.9700 . ?
C6 C19 1.505(7) . ?
C6 H22 0.9800 . ?
C8 C9 1.554(6) . ?
C8 H14 0.9800 . ?
C9 C10 1.494(7) . ?
C9 H19 0.9800 . ?
C10 C11 1.360(8) . ?
C10 C27 1.370(8) . ?
C11 C12 1.405(13) . ?
C11 H18 0.9300 . ?
C12 C13 1.358(16) . ?
C12 H17 0.9300 . ?
C13 C26 1.346(14) . ?
C13 H1 0.9300 . ?
C14 C15 1.374(13) . ?
C14 H4 0.9300 . ?
C15 H5 0.9300 . ?
C16 C28 1.517(10) . ?
C16 C17 1.523(11) . ?
C16 H24 0.9800 . ?
C17 C18 1.443(13) . ?
C18 C19 1.328(9) . ?
C18 H23 0.9300 . ?
C19 H8 0.9300 . ?
C21 C22 1.379(7) . ?
C21 H9 0.9300 . ?
C22 C23 1.368(8) . ?
C22 H13 0.9300 . ?
C23 C24 1.361(9) . ?
C23 H12 0.9300 . ?
C24 C25 1.373(8) . ?
C24 H10 0.9300 . ?
C25 H11 0.9300 . ?
C26 C27 1.387(10) . ?
C26 H16 0.9300 . ?
C27 H15 0.9300 . ?
C28 H21 0.9700 . ?
C28 H20 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
C20 O2 C9 111.1(3) . . ?
C5 N1 C6 119.3(6) . . ?
C5 N1 C16 112.7(5) . . ?
C6 N1 C16 101.5(4) . . ?
C20 N3 C7 125.2(4) . . ?
C20 N3 C8 110.5(4) . . ?
C7 N3 C8 119.9(4) . . ?
C15 C1 C2 120.9(8) . . ?
C15 C1 Cl1 118.0(7) . . ?
C2 C1 Cl1 121.1(8) . . ?
C7 C2A C28 113.7(4) . . ?
C7 C2A C6 111.9(4) . . ?
C28 C2A C6 102.6(5) . . ?
C7 C2A H2A 109.5 . . ?
C28 C2A H2A 109.5 . . ?
C6 C2A H2A 109.5 . . ?
C1 C2 C3 116.8(8) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 123.6(7) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C21 C4A C25 117.9(5) . . ?
C21 C4A C8 124.1(4) . . ?
C25 C4A C8 118.0(4) . . ?
C14 C4 C3 116.1(8) . . ?
C14 C4 C5 122.6(8) . . ?
C3 C4 C5 121.3(7) . . ?
N1 C5 C4 113.3(5) . . ?
N1 C5 H6 108.9 . . ?
C4 C5 H6 108.9 . . ?
N1 C5 H7 108.9 . . ?
C4 C5 H7 108.9 . . ?
H6 C5 H7 107.7 . . ?
N1 C6 C19 114.3(4) . . ?
N1 C6 C2A 99.4(4) . . ?
C19 C6 C2A 107.7(5) . . ?
N1 C6 H22 111.6 . . ?
C19 C6 H22 111.6 . . ?
C2A C6 H22 111.6 . . ?
O4 C7 N3 118.6(4) . . ?
O4 C7 C2A 124.4(4) . . ?
N3 C7 C2A 117.0(4) . . ?
N3 C8 C4A 116.3(4) . . ?
N3 C8 C9 99.9(3) . . ?
C4A C8 C9 114.6(4) . . ?
N3 C8 H14 108.5 . . ?
C4A C8 H14 108.5 . . ?
C9 C8 H14 108.5 . . ?
O2 C9 C10 108.8(4) . . ?
O2 C9 C8 103.2(3) . . ?
C10 C9 C8 117.3(4) . . ?
O2 C9 H19 109.1 . . ?
C10 C9 H19 109.1 . . ?
C8 C9 H19 109.1 . . ?
C11 C10 C27 118.3(6) . . ?
C11 C10 C9 119.2(5) . . ?
C27 C10 C9 122.4(5) . . ?
C10 C11 C12 119.7(9) . . ?
C10 C11 H18 120.1 . . ?
C12 C11 H18 120.1 . . ?
C13 C12 C11 120.3(9) . . ?
C13 C12 H17 119.8 . . ?
C11 C12 H17 119.8 . . ?
C26 C13 C12 120.6(9) . . ?
C26 C13 H1 119.7 . . ?
C12 C13 H1 119.7 . . ?
C4 C14 C15 122.2(8) . . ?
C4 C14 H4 118.9 . . ?
C15 C14 H4 118.9 . . ?
C1 C15 C14 120.5(8) . . ?
C1 C15 H5 119.8 . . ?
C14 C15 H5 119.8 . . ?
N1 C16 C28 99.9(5) . . ?
N1 C16 C17 112.0(6) . . ?
C28 C16 C17 111.0(6) . . ?
N1 C16 H24 111.1 . . ?
C28 C16 H24 111.1 . . ?
C17 C16 H24 111.1 . . ?
O1 C17 C18 121.9(8) . . ?
O1 C17 C16 122.3(8) . . ?
C18 C17 C16 115.6(6) . . ?
C19 C18 C17 119.4(7) . . ?
C19 C18 H23 120.3 . . ?
C17 C18 H23 120.3 . . ?
C18 C19 C6 120.1(6) . . ?
C18 C19 H8 119.9 . . ?
C6 C19 H8 119.9 . . ?
O3 C20 O2 122.8(4) . . ?
O3 C20 N3 128.3(5) . . ?
O2 C20 N3 108.9(4) . . ?
C22 C21 C4A 120.3(5) . . ?
C22 C21 H9 119.8 . . ?
C4A C21 H9 119.8 . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 H13 119.7 . . ?
C21 C22 H13 119.7 . . ?
C24 C23 C22 119.9(5) . . ?
C24 C23 H12 120.1 . . ?
C22 C23 H12 120.1 . . ?
C23 C24 C25 120.6(5) . . ?
C23 C24 H10 119.7 . . ?
C25 C24 H10 119.7 . . ?
C24 C25 C4A 120.7(5) . . ?
C24 C25 H11 119.7 . . ?
C4A C25 H11 119.7 . . ?
C13 C26 C27 118.7(9) . . ?
C13 C26 H16 120.6 . . ?
C27 C26 H16 120.6 . . ?
C10 C27 C26 122.3(7) . . ?
C10 C27 H15 118.9 . . ?
C26 C27 H15 118.9 . . ?
C16 C28 C2A 105.5(5) . . ?
C16 C28 H21 110.7 . . ?
C2A C28 H21 110.7 . . ?
C16 C28 H20 110.7 . . ?
C2A C28 H20 110.7 . . ?
H21 C28 H20 108.8 . . ?

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
C15 C1 C2 C3 2.0(13) . . . . ?
Cl1 C1 C2 C3 -179.3(6) . . . . ?
C1 C2 C3 C4 -1.8(13) . . . . ?
C2 C3 C4 C14 1.5(11) . . . . ?
C2 C3 C4 C5 -175.1(7) . . . . ?
C6 N1 C5 C4 -63.8(9) . . . . ?
C16 N1 C5 C4 177.3(6) . . . . ?
C14 C4 C5 N1 107.1(8) . . . . ?
C3 C4 C5 N1 -76.4(9) . . . . ?
C5 N1 C6 C19 -64.3(7) . . . . ?
C16 N1 C6 C19 60.2(7) . . . . ?
C5 N1 C6 C2A -178.7(5) . . . . ?
C16 N1 C6 C2A -54.2(5) . . . . ?
C7 C2A C6 N1 -88.3(4) . . . . ?
C28 C2A C6 N1 34.0(5) . . . . ?
C7 C2A C6 C19 152.3(4) . . . . ?
C28 C2A C6 C19 -85.4(5) . . . . ?
C20 N3 C7 O4 153.9(5) . . . . ?
C8 N3 C7 O4 -0.1(6) . . . . ?
C20 N3 C7 C2A -26.9(7) . . . . ?
C8 N3 C7 C2A 179.1(4) . . . . ?
C28 C2A C7 O4 5.3(7) . . . . ?
C6 C2A C7 O4 120.9(5) . . . . ?
C28 C2A C7 N3 -173.8(4) . . . . ?
C6 C2A C7 N3 -58.2(5) . . . . ?
C20 N3 C8 C4A 143.6(4) . . . . ?
C7 N3 C8 C4A -58.9(6) . . . . ?
C20 N3 C8 C9 19.7(5) . . . . ?
C7 N3 C8 C9 177.2(4) . . . . ?
C21 C4A C8 N3 -26.8(7) . . . . ?
C25 C4A C8 N3 153.8(4) . . . . ?
C21 C4A C8 C9 89.1(6) . . . . ?
C25 C4A C8 C9 -90.2(5) . . . . ?
C20 O2 C9 C10 -102.9(4) . . . . ?
C20 O2 C9 C8 22.3(5) . . . . ?
N3 C8 C9 O2 -24.0(4) . . . . ?
C4A C8 C9 O2 -149.1(4) . . . . ?
N3 C8 C9 C10 95.5(5) . . . . ?
C4A C8 C9 C10 -29.6(6) . . . . ?
O2 C9 C10 C11 -139.0(6) . . . . ?
C8 C9 C10 C11 104.4(6) . . . . ?
O2 C9 C10 C27 38.1(7) . . . . ?
C8 C9 C10 C27 -78.5(7) . . . . ?
C27 C10 C11 C12 0.6(12) . . . . ?
C9 C10 C11 C12 177.8(8) . . . . ?
C10 C11 C12 C13 -0.1(18) . . . . ?
C11 C12 C13 C26 0(2) . . . . ?
C3 C4 C14 C15 -1.4(12) . . . . ?
C5 C4 C14 C15 175.2(8) . . . . ?
C2 C1 C15 C14 -2.0(14) . . . . ?
Cl1 C1 C15 C14 179.3(7) . . . . ?
C4 C14 C15 C1 1.7(14) . . . . ?
C5 N1 C16 C28 -178.9(6) . . . . ?
C6 N1 C16 C28 52.3(5) . . . . ?
C5 N1 C16 C17 63.5(8) . . . . ?
C6 N1 C16 C17 -65.3(7) . . . . ?
N1 C16 C17 O1 -144.8(8) . . . . ?
C28 C16 C17 O1 104.5(10) . . . . ?
N1 C16 C17 C18 39.7(10) . . . . ?
C28 C16 C17 C18 -71.0(9) . . . . ?
O1 C17 C18 C19 -178.5(9) . . . . ?
C16 C17 C18 C19 -2.9(13) . . . . ?
C17 C18 C19 C6 -2.7(13) . . . . ?
N1 C6 C19 C18 -28.7(10) . . . . ?
C2A C6 C19 C18 80.7(8) . . . . ?
C9 O2 C20 O3 170.7(4) . . . . ?
C9 O2 C20 N3 -10.3(5) . . . . ?
C7 N3 C20 O3 15.6(8) . . . . ?
C8 N3 C20 O3 171.7(5) . . . . ?
C7 N3 C20 O2 -163.3(4) . . . . ?
C8 N3 C20 O2 -7.3(5) . . . . ?
C25 C4A C21 C22 1.5(8) . . . . ?
C8 C4A C21 C22 -177.8(5) . . . . ?
C4A C21 C22 C23 -0.3(9) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
C22 C23 C24 C25 -0.4(8) . . . . ?
C23 C24 C25 C4A 1.6(8) . . . . ?
C21 C4A C25 C24 -2.2(7) . . . . ?
C8 C4A C25 C24 177.2(4) . . . . ?
C12 C13 C26 C27 0.4(18) . . . . ?
C11 C10 C27 C26 -0.6(10) . . . . ?
C9 C10 C27 C26 -177.7(6) . . . . ?
C13 C26 C27 C10 0.1(13) . . . . ?
N1 C16 C28 C2A -28.9(6) . . . . ?
C17 C16 C28 C2A 89.4(6) . . . . ?
C7 C2A C28 C16 118.0(5) . . . . ?
C6 C2A C28 C16 -3.0(5) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_cu_20230612ZYW03262_0m
_database_code_depnum_ccdc_archive 'CCDC 2395527'
loop_
_audit_author_name
_audit_author_address
'Xiaodi Yang'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-03 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 Cl N2 O4'
_chemical_formula_weight         436.88

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.5846(3)
_cell_length_b                   6.2016(2)
_cell_length_c                   13.8899(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.423(2)
_cell_angle_gamma                90
_cell_volume                     1077.23(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    6419
_cell_measurement_theta_min      3.2018
_cell_measurement_theta_max      65.0590

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.852
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16849
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_max         65.388
_diffrn_reflns_theta_full        65.388
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3692
_reflns_number_gt                2953
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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)+(0.0510P)²+0.2176P] 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_abs_structure_details 
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3692
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.71783(11) 0.5416(5) 0.13011(15) 0.1527(11) Uani 1 1 d . . . . .
O1 O 0.0373(3) 0.3451(6) 0.4922(3) 0.0811(10) Uani 1 1 d . . . . .
O2 O 0.2171(2) 0.8656(5) 0.4115(2) 0.0692(8) Uani 1 1 d . . . . .
O3F O 0.0994(3) 0.4645(7) 0.6390(2) 0.0840(10) Uani 1 1 d . . . . .
O3 O 0.0955(4) 0.1353(6) 0.1001(3) 0.1104(14) Uani 1 1 d . . . . .
N1 N 0.2108(2) 0.6047(6) 0.2110(2) 0.0557(8) Uani 1 1 d . . . . .
N2 N 0.1641(2) 0.6177(6) 0.5127(2) 0.0524(8) Uani 1 1 d . . . . .
C1 C 0.5804(4) 0.5796(12) 0.1254(4) 0.0855(17) Uani 1 1 d . . . . .
C2 C 0.5126(4) 0.4257(10) 0.0848(4) 0.0843(17) Uani 1 1 d . . . . .
H21 H 0.539273 0.300376 0.059650 0.101 Uiso 1 1 calc R U . . .
C3 C 0.4033(4) 0.4578(8) 0.0813(3) 0.0683(12) Uani 1 1 d . . . . .
H2 H 0.356710 0.352839 0.053672 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3622(3) 0.6433(8) 0.1183(3) 0.0599(10) Uani 1 1 d . . . . .
C5 C 0.2444(3) 0.6771(8) 0.1180(3) 0.0673(12) Uani 1 1 d . . . . .
H3 H 0.227455 0.828685 0.108204 0.081 Uiso 1 1 calc R U . . .
H18 H 0.206123 0.596263 0.065231 0.081 Uiso 1 1 calc R U . . .
C6 C 0.1125(3) 0.7050(7) 0.2402(3) 0.0537(9) Uani 1 1 d . . . . .
H4 H 0.121121 0.860763 0.249907 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1033(3) 0.5869(6) 0.3361(3) 0.0496(9) Uani 1 1 d . . . . .
H12 H 0.027949 0.576573 0.347269 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1655(3) 0.7025(7) 0.4200(3) 0.0517(9) Uani 1 1 d . . . . .
C9 C 0.2215(3) 0.7312(8) 0.5956(3) 0.0610(11) Uani 1 1 d . . . . .
H6 H 0.206828 0.886195 0.590603 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3411(3) 0.6917(7) 0.6044(3) 0.0530(9) Uani 1 1 d . . . . .
C11 C 0.4094(3) 0.8521(8) 0.6419(3) 0.0609(10) Uani 1 1 d . . . . .
H10 H 0.381535 0.984035 0.658740 0.073 Uiso 1 1 calc R U . . .
C12 C 0.5191(3) 0.8195(8) 0.6548(3) 0.0666(12) Uani 1 1 d . . . . .
H9 H 0.564387 0.928367 0.680735 0.080 Uiso 1 1 calc R U . . .
C13 C 0.5604(3) 0.6262(9) 0.6292(3) 0.0629(11) Uani 1 1 d . . . . .
H1 H 0.633929 0.604197 0.637975 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0940(3) 0.4663(8) 0.5415(3) 0.0640(11) Uani 1 1 d . . . . .
C15 C 0.1672(4) 0.6341(11) 0.6796(4) 0.0830(16) Uani 1 1 d . . . . .
H11 H 0.220389 0.577816 0.729116 0.100 Uiso 1 1 calc R U . . .
H5 H 0.125446 0.743007 0.708490 0.100 Uiso 1 1 calc R U . . .
C16 C 0.4938(3) 0.4637(8) 0.5905(3) 0.0622(10) Uani 1 1 d . . . . .
H8 H 0.522026 0.332906 0.572747 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3833(3) 0.4982(7) 0.5783(3) 0.0605(10) Uani 1 1 d . . . . .
H7 H 0.337909 0.389501 0.552278 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1477(3) 0.3578(7) 0.3182(3) 0.0559(9) Uani 1 1 d . . . . .
H14 H 0.206362 0.321525 0.366798 0.067 Uiso 1 1 calc R U . . .
H13 H 0.092140 0.249471 0.318898 0.067 Uiso 1 1 calc R U . . .
C19 C 0.1861(3) 0.3751(7) 0.2173(3) 0.0582(10) Uani 1 1 d . . . . .
H15 H 0.249828 0.286525 0.212980 0.070 Uiso 1 1 calc R U . . .
C20 C 0.0962(4) 0.3112(8) 0.1405(3) 0.0720(12) Uani 1 1 d . . . . .
C21 C 0.0098(4) 0.4679(9) 0.1214(3) 0.0740(13) Uani 1 1 d . . . . .
H16 H -0.048762 0.438179 0.076417 0.089 Uiso 1 1 calc R U . . .
C22 C 0.0163(3) 0.6533(8) 0.1694(3) 0.0665(12) Uani 1 1 d . . . . .
H17 H -0.039224 0.752606 0.159126 0.080 Uiso 1 1 calc R U . . .
C23 C 0.4339(4) 0.7958(9) 0.1592(3) 0.0735(13) Uani 1 1 d . . . . .
H19 H 0.408060 0.921261 0.184872 0.088 Uiso 1 1 calc R U . . .
C24 C 0.5430(4) 0.7657(11) 0.1626(4) 0.0900(18) Uani 1 1 d . . . . .
H20 H 0.590222 0.870073 0.189758 0.108 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
Cl1 C1 1.740(5) . ?
O1 C14 1.197(6) . ?
O2 C8 1.215(5) . ?
O3F C14 1.348(5) . ?
O3F C15 1.429(7) . ?
O3 C20 1.226(6) . ?
N1 C19 1.463(6) . ?
N1 C5 1.473(5) . ?
N1 C6 1.481(5) . ?
N2 C14 1.378(6) . ?
N2 C8 1.393(5) . ?
N2 C9 1.470(5) . ?
C1 C2 1.360(9) . ?
C1 C24 1.369(9) . ?
C2 C3 1.385(7) . ?
C2 H21 0.9300 . ?
C3 C4 1.383(7) . ?
C3 H2 0.9300 . ?
C4 C23 1.384(7) . ?
C4 C5 1.498(6) . ?
C5 H3 0.9700 . ?
C5 H18 0.9700 . ?
C6 C22 1.506(6) . ?
C6 C7 1.536(5) . ?
C6 H4 0.9800 . ?
C7 C8 1.510(6) . ?
C7 C18 1.557(5) . ?
C7 H12 0.9800 . ?
C9 C10 1.516(5) . ?
C9 C15 1.538(6) . ?
C9 H6 0.9800 . ?
C10 C17 1.377(6) . ?
C10 C11 1.378(6) . ?
C11 C12 1.387(6) . ?
C11 H10 0.9300 . ?
C12 C13 1.369(7) . ?
C12 H9 0.9300 . ?
C13 C16 1.381(7) . ?
C13 H1 0.9300 . ?
C15 H11 0.9700 . ?
C15 H5 0.9700 . ?
C16 C17 1.398(6) . ?
C16 H8 0.9300 . ?
C17 H7 0.9300 . ?
C18 C19 1.535(6) . ?
C18 H14 0.9700 . ?
C18 H13 0.9700 . ?
C19 C20 1.518(6) . ?
C19 H15 0.9800 . ?
C20 C21 1.460(7) . ?
C21 C22 1.327(7) . ?
C21 H16 0.9300 . ?
C22 H17 0.9300 . ?
C23 C24 1.380(7) . ?
C23 H19 0.9300 . ?
C24 H20 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
C14 O3F C15 110.5(4) . . ?
C19 N1 C5 115.7(4) . . ?
C19 N1 C6 101.7(3) . . ?
C5 N1 C6 116.3(3) . . ?
C14 N2 C8 126.9(3) . . ?
C14 N2 C9 111.9(3) . . ?
C8 N2 C9 119.2(3) . . ?
C2 C1 C24 121.4(5) . . ?
C2 C1 Cl1 119.7(5) . . ?
C24 C1 Cl1 118.8(5) . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 H21 120.4 . . ?
C3 C2 H21 120.4 . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 H2 119.4 . . ?
C2 C3 H2 119.4 . . ?
C3 C4 C23 117.8(4) . . ?
C3 C4 C5 121.7(4) . . ?
C23 C4 C5 120.4(4) . . ?
N1 C5 C4 109.6(3) . . ?
N1 C5 H3 109.7 . . ?
C4 C5 H3 109.7 . . ?
N1 C5 H18 109.7 . . ?
C4 C5 H18 109.7 . . ?
H3 C5 H18 108.2 . . ?
N1 C6 C22 111.5(3) . . ?
N1 C6 C7 100.6(3) . . ?
C22 C6 C7 109.4(3) . . ?
N1 C6 H4 111.6 . . ?
C22 C6 H4 111.6 . . ?
C7 C6 H4 111.6 . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 C18 113.1(3) . . ?
C6 C7 C18 103.5(3) . . ?
C8 C7 H12 109.6 . . ?
C6 C7 H12 109.6 . . ?
C18 C7 H12 109.6 . . ?
O2 C8 N2 117.8(4) . . ?
O2 C8 C7 123.9(4) . . ?
N2 C8 C7 118.3(3) . . ?
N2 C9 C10 112.5(3) . . ?
N2 C9 C15 100.7(4) . . ?
C10 C9 C15 113.4(4) . . ?
N2 C9 H6 110.0 . . ?
C10 C9 H6 110.0 . . ?
C15 C9 H6 110.0 . . ?
C17 C10 C11 119.1(4) . . ?
C17 C10 C9 121.9(4) . . ?
C11 C10 C9 119.0(4) . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H10 119.6 . . ?
C12 C11 H10 119.6 . . ?
C13 C12 C11 119.7(4) . . ?
C13 C12 H9 120.1 . . ?
C11 C12 H9 120.1 . . ?
C12 C13 C16 120.6(4) . . ?
C12 C13 H1 119.7 . . ?
C16 C13 H1 119.7 . . ?
O1 C14 O3F 122.0(4) . . ?
O1 C14 N2 128.4(4) . . ?
O3F C14 N2 109.6(4) . . ?
O3F C15 C9 106.6(4) . . ?
O3F C15 H11 110.4 . . ?
C9 C15 H11 110.4 . . ?
O3F C15 H5 110.4 . . ?
C9 C15 H5 110.4 . . ?
H11 C15 H5 108.6 . . ?
C13 C16 C17 119.2(4) . . ?
C13 C16 H8 120.4 . . ?
C17 C16 H8 120.4 . . ?
C10 C17 C16 120.6(4) . . ?
C10 C17 H7 119.7 . . ?
C16 C17 H7 119.7 . . ?
C19 C18 C7 103.7(3) . . ?
C19 C18 H14 111.0 . . ?
C7 C18 H14 111.0 . . ?
C19 C18 H13 111.0 . . ?
C7 C18 H13 111.0 . . ?
H14 C18 H13 109.0 . . ?
N1 C19 C20 111.0(4) . . ?
N1 C19 C18 102.4(3) . . ?
C20 C19 C18 109.7(4) . . ?
N1 C19 H15 111.1 . . ?
C20 C19 H15 111.1 . . ?
C18 C19 H15 111.1 . . ?
O3 C20 C21 122.8(5) . . ?
O3 C20 C19 121.4(5) . . ?
C21 C20 C19 115.8(4) . . ?
C22 C21 C20 118.9(4) . . ?
C22 C21 H16 120.6 . . ?
C20 C21 H16 120.6 . . ?
C21 C22 C6 120.8(4) . . ?
C21 C22 H17 119.6 . . ?
C6 C22 H17 119.6 . . ?
C24 C23 C4 121.4(5) . . ?
C24 C23 H19 119.3 . . ?
C4 C23 H19 119.3 . . ?
C1 C24 C23 118.9(5) . . ?
C1 C24 H20 120.5 . . ?
C23 C24 H20 120.5 . . ?

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
C24 C1 C2 C3 -0.2(8) . . . . ?
Cl1 C1 C2 C3 -179.9(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C2 C3 C4 C23 -0.2(6) . . . . ?
C2 C3 C4 C5 -178.0(4) . . . . ?
C19 N1 C5 C4 -85.6(5) . . . . ?
C6 N1 C5 C4 155.2(4) . . . . ?
C3 C4 C5 N1 93.7(5) . . . . ?
C23 C4 C5 N1 -84.1(5) . . . . ?
C19 N1 C6 C22 -63.8(4) . . . . ?
C5 N1 C6 C22 62.8(5) . . . . ?
C19 N1 C6 C7 52.1(4) . . . . ?
C5 N1 C6 C7 178.7(3) . . . . ?
N1 C6 C7 C8 88.0(3) . . . . ?
C22 C6 C7 C8 -154.5(3) . . . . ?
N1 C6 C7 C18 -33.7(4) . . . . ?
C22 C6 C7 C18 83.8(4) . . . . ?
C14 N2 C8 O2 164.6(4) . . . . ?
C9 N2 C8 O2 1.9(5) . . . . ?
C14 N2 C8 C7 -15.6(6) . . . . ?
C9 N2 C8 C7 -178.3(3) . . . . ?
C6 C7 C8 O2 -1.1(5) . . . . ?
C18 C7 C8 O2 114.8(4) . . . . ?
C6 C7 C8 N2 179.1(3) . . . . ?
C18 C7 C8 N2 -65.1(4) . . . . ?
C14 N2 C9 C10 116.8(4) . . . . ?
C8 N2 C9 C10 -78.1(5) . . . . ?
C14 N2 C9 C15 -4.3(5) . . . . ?
C8 N2 C9 C15 160.9(4) . . . . ?
N2 C9 C10 C17 -33.3(6) . . . . ?
C15 C9 C10 C17 80.1(5) . . . . ?
N2 C9 C10 C11 148.3(4) . . . . ?
C15 C9 C10 C11 -98.2(5) . . . . ?
C17 C10 C11 C12 -1.0(6) . . . . ?
C9 C10 C11 C12 177.4(4) . . . . ?
C10 C11 C12 C13 0.6(7) . . . . ?
C11 C12 C13 C16 0.1(7) . . . . ?
C15 O3F C14 O1 -176.1(5) . . . . ?
C15 O3F C14 N2 6.0(5) . . . . ?
C8 N2 C14 O1 17.8(8) . . . . ?
C9 N2 C14 O1 -178.4(5) . . . . ?
C8 N2 C14 O3F -164.5(4) . . . . ?
C9 N2 C14 O3F -0.7(5) . . . . ?
C14 O3F C15 C9 -8.6(5) . . . . ?
N2 C9 C15 O3F 7.5(5) . . . . ?
C10 C9 C15 O3F -112.9(4) . . . . ?
C12 C13 C16 C17 -0.4(7) . . . . ?
C11 C10 C17 C16 0.7(6) . . . . ?
C9 C10 C17 C16 -177.6(4) . . . . ?
C13 C16 C17 C10 0.0(6) . . . . ?
C8 C7 C18 C19 -115.8(4) . . . . ?
C6 C7 C18 C19 4.6(4) . . . . ?
C5 N1 C19 C20 -59.4(4) . . . . ?
C6 N1 C19 C20 67.5(4) . . . . ?
C5 N1 C19 C18 -176.4(3) . . . . ?
C6 N1 C19 C18 -49.5(4) . . . . ?
C7 C18 C19 N1 26.8(4) . . . . ?
C7 C18 C19 C20 -91.2(4) . . . . ?
N1 C19 C20 O3 143.8(5) . . . . ?
C18 C19 C20 O3 -103.8(6) . . . . ?
N1 C19 C20 C21 -38.8(5) . . . . ?
C18 C19 C20 C21 73.6(5) . . . . ?
O3 C20 C21 C22 179.0(5) . . . . ?
C19 C20 C21 C22 1.6(7) . . . . ?
C20 C21 C22 C6 1.8(7) . . . . ?
N1 C6 C22 C21 31.3(6) . . . . ?
C7 C6 C22 C21 -79.0(5) . . . . ?
C3 C4 C23 C24 0.4(7) . . . . ?
C5 C4 C23 C24 178.3(4) . . . . ?
C2 C1 C24 C23 0.5(8) . . . . ?
Cl1 C1 C24 C23 -179.8(4) . . . . ?
C4 C23 C24 C1 -0.6(8) . . . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043

