# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_230804hzs5f_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2hnprm
_database_code_depnum_ccdc_archive 'CCDC 2313801'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.mtchem.2024.102042 2024
loop_
_audit_author_name
_audit_author_address
TFM
;Southern medical university
China
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F6 N2 O4'
_chemical_formula_sum            'C22 H18 F6 N2 O4'
_chemical_formula_weight         488.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.443(2)
_cell_length_b                   10.421(2)
_cell_length_c                   12.024(3)
_cell_angle_alpha                107.595(4)
_cell_angle_beta                 96.454(4)
_cell_angle_gamma                113.967(3)
_cell_volume                     1097.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2877
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.555
_cell_measurement_theta_min      2.316
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0524 before and 0.0234 after correction.
The Ratio of minimum to maximum transmission is 0.9198.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6658
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_min         2.801
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3522
_reflns_number_total             4796
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.088(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4796
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.3610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1254
_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
F1 \\sim F2 \\sim F3 \\sim C11 \\sim F1A \\sim F3A \\sim F2A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F4 \\sim F5 \\sim F6 \\sim C22 \\sim F5A \\sim F4A \\sim F6A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(F1A)=Sof(F3A)=Sof(F2A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F5A)=Sof(F4A)=Sof(F6A)=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C17(H17), C18(H18), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0544(9) -0.2107(4) 0.8688(5) 0.145(2) Uani 0.643(5) 1 d . U P A 1
F2 F 0.0201(8) -0.3246(6) 0.6816(6) 0.1246(19) Uani 0.643(5) 1 d . U P A 1
F3 F -0.1538(4) -0.3341(4) 0.7528(7) 0.1135(15) Uani 0.643(5) 1 d . U P A 1
F4 F 0.6195(5) 0.1271(8) 0.3827(3) 0.148(3) Uani 0.662(5) 1 d . U P B 1
F5 F 0.7081(5) 0.1392(5) 0.5533(4) 0.1206(14) Uani 0.662(5) 1 d . U P B 1
F6 F 0.7989(5) 0.3271(5) 0.5070(6) 0.128(2) Uani 0.662(5) 1 d . U P B 1
O1 O 0.20110(17) 0.66013(16) 1.05898(14) 0.0728(5) Uani 1 1 d . . . . .
O2 O 0.38262(15) 0.80711(13) 1.00272(11) 0.0572(4) Uani 1 1 d . . . . .
O3 O 0.54842(13) 0.65095(14) 0.96738(10) 0.0526(3) Uani 1 1 d . . . . .
O4 O 0.56782(13) 0.73398(13) 0.81549(11) 0.0504(3) Uani 1 1 d . . . . .
N1 N 0.05774(14) 0.30812(15) 0.71089(13) 0.0429(3) Uani 1 1 d . . . . .
N2 N 0.29930(14) 0.44217(15) 0.69343(12) 0.0399(3) Uani 1 1 d . . . . .
C1 C 0.14222(18) 0.36476(19) 0.63406(16) 0.0456(4) Uani 1 1 d . . . . .
H1A H 0.114765 0.436740 0.613198 0.055 Uiso 1 1 calc R U . . .
H1B H 0.119913 0.279063 0.557831 0.055 Uiso 1 1 calc R U . . .
C2 C 0.07771(18) 0.43342(18) 0.81963(17) 0.0477(4) Uani 1 1 d . . . . .
H2A H 0.046171 0.393794 0.882296 0.057 Uiso 1 1 calc R U . . .
H2B H 0.016424 0.479406 0.799779 0.057 Uiso 1 1 calc R U . . .
C3 C 0.23566(17) 0.55365(17) 0.86881(15) 0.0396(4) Uani 1 1 d . . . . .
C4 C 0.33717(17) 0.54588(16) 0.81066(14) 0.0365(3) Uani 1 1 d . . . . .
C5 C 0.03676(16) 0.16977(17) 0.71835(14) 0.0385(4) Uani 1 1 d . . . . .
C6 C 0.09906(18) 0.08447(18) 0.65637(15) 0.0425(4) Uani 1 1 d . . . . .
H6 H 0.155843 0.118670 0.605076 0.051 Uiso 1 1 calc R U . . .
C7 C 0.07874(19) -0.04956(18) 0.66906(16) 0.0467(4) Uani 1 1 d . . . . .
H7 H 0.122614 -0.105958 0.626971 0.056 Uiso 1 1 calc R U . . .
C8 C -0.00426(19) -0.10218(18) 0.74195(16) 0.0473(4) Uani 1 1 d . . . . .
C9 C -0.0719(2) -0.0218(2) 0.79962(19) 0.0549(5) Uani 1 1 d . . . . .
H9 H -0.132396 -0.059281 0.847637 0.066 Uiso 1 1 calc R U . . .
C10 C -0.05207(19) 0.11199(19) 0.78784(18) 0.0498(4) Uani 1 1 d . . . . .
H10 H -0.099525 0.165595 0.827559 0.060 Uiso 1 1 calc R U . . .
C11 C -0.0177(3) -0.2406(2) 0.7608(2) 0.0678(6) Uani 1 1 d . U . . .
C12 C 0.26968(19) 0.67529(18) 0.98594(16) 0.0442(4) Uani 1 1 d . . . . .
C13 C 0.4331(3) 0.9268(2) 1.1213(2) 0.0838(8) Uani 1 1 d . . . . .
H13A H 0.519618 1.015375 1.124801 0.126 Uiso 1 1 calc R U . . .
H13B H 0.457655 0.890790 1.182944 0.126 Uiso 1 1 calc R U . . .
H13C H 0.356236 0.955373 1.136419 0.126 Uiso 1 1 calc R U . . .
C14 C 0.49728(17) 0.65626(17) 0.86349(14) 0.0379(3) Uani 1 1 d . . . . .
C15 C 0.7012(2) 0.7515(3) 1.0250(2) 0.0924(9) Uani 1 1 d . . . . .
H15A H 0.758419 0.722330 0.972877 0.139 Uiso 1 1 calc R U . . .
H15B H 0.727500 0.744422 1.102989 0.139 Uiso 1 1 calc R U . . .
H15C H 0.721403 0.856277 1.038452 0.139 Uiso 1 1 calc R U . . .
C16 C 0.39180(17) 0.38500(16) 0.64559(13) 0.0364(3) Uani 1 1 d . . . . .
C17 C 0.49403(18) 0.37111(18) 0.71873(15) 0.0426(4) Uani 1 1 d . . . . .
H17 H 0.501549 0.397914 0.802925 0.051 Uiso 1 1 calc R U . . .
C18 C 0.5849(2) 0.3183(2) 0.66926(16) 0.0493(4) Uani 1 1 d . . . . .
H18 H 0.657095 0.312311 0.720017 0.059 Uiso 1 1 calc R U . . .
C19 C 0.5711(2) 0.2743(2) 0.54615(17) 0.0511(4) Uani 1 1 d . . . . .
C20 C 0.4669(2) 0.2839(2) 0.47245(16) 0.0540(5) Uani 1 1 d . . . . .
H20 H 0.455907 0.251398 0.387572 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3789(2) 0.3405(2) 0.52192(15) 0.0470(4) Uani 1 1 d . . . . .
H21 H 0.308911 0.349145 0.471125 0.056 Uiso 1 1 calc R U . . .
C22 C 0.6701(3) 0.2187(3) 0.4931(2) 0.0778(7) Uani 1 1 d . U . . .
F1A F -0.0646(15) -0.2625(11) 0.8491(10) 0.115(3) Uani 0.357(5) 1 d . U P A 2
F3A F -0.0885(14) -0.3638(6) 0.6669(8) 0.132(4) Uani 0.357(5) 1 d . U P A 2
F2A F 0.1133(7) -0.2369(10) 0.7846(12) 0.112(2) Uani 0.357(5) 1 d . U P A 2
F5A F 0.6048(11) 0.0771(7) 0.4345(10) 0.118(3) Uani 0.338(5) 1 d . U P B 2
F4A F 0.7002(10) 0.2684(12) 0.3973(9) 0.119(2) Uani 0.338(5) 1 d . U P B 2
F6A F 0.7871(9) 0.2698(15) 0.5590(7) 0.130(4) Uani 0.338(5) 1 d . U P B 2


_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
F1 C11 1.301(4) . ?
F2 C11 1.301(4) . ?
F3 C11 1.329(4) . ?
F4 C22 1.272(4) . ?
F5 C22 1.391(4) . ?
F6 C22 1.309(4) . ?
O1 C12 1.201(2) . ?
O2 C12 1.335(2) . ?
O2 C13 1.445(2) . ?
O3 C14 1.3284(19) . ?
O3 C15 1.441(2) . ?
O4 C14 1.1939(19) . ?
N1 C1 1.439(2) . ?
N1 C2 1.464(2) . ?
N1 C5 1.400(2) . ?
N2 C1 1.471(2) . ?
N2 C4 1.3848(19) . ?
N2 C16 1.416(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.515(2) . ?
C3 C4 1.350(2) . ?
C3 C12 1.469(2) . ?
C4 C14 1.510(2) . ?
C5 C6 1.395(2) . ?
C5 C10 1.395(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(3) . ?
C8 C9 1.386(3) . ?
C8 C11 1.481(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(2) . ?
C10 H10 0.9500 . ?
C11 F1A 1.261(6) . ?
C11 F3A 1.279(6) . ?
C11 F2A 1.349(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.388(2) . ?
C16 C21 1.390(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 C20 1.379(3) . ?
C19 C22 1.491(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9500 . ?
C22 F5A 1.259(7) . ?
C22 F4A 1.416(6) . ?
C22 F6A 1.185(6) . ?

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
C12 O2 C13 116.56(15) . . ?
C14 O3 C15 115.31(15) . . ?
C1 N1 C2 110.79(13) . . ?
C5 N1 C1 120.03(14) . . ?
C5 N1 C2 119.46(14) . . ?
C4 N2 C1 113.38(13) . . ?
C4 N2 C16 123.67(13) . . ?
C16 N2 C1 120.94(13) . . ?
N1 C1 N2 111.59(13) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N2 C1 H1A 109.3 . . ?
N2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 C3 110.79(13) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C4 C3 C2 122.12(14) . . ?
C4 C3 C12 123.08(15) . . ?
C12 C3 C2 114.76(14) . . ?
N2 C4 C14 115.20(13) . . ?
C3 C4 N2 121.63(14) . . ?
C3 C4 C14 122.98(14) . . ?
C6 C5 N1 122.46(15) . . ?
C10 C5 N1 119.43(15) . . ?
C10 C5 C6 118.09(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.50(16) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.81(16) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 119.13(16) . . ?
C7 C8 C11 120.31(17) . . ?
C9 C8 C11 120.54(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.48(17) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.87(16) . . ?
C9 C10 H10 119.6 . . ?
F1 C11 F3 103.9(4) . . ?
F1 C11 C8 112.7(2) . . ?
F2 C11 F1 108.6(4) . . ?
F2 C11 F3 104.0(3) . . ?
F2 C11 C8 114.2(2) . . ?
F3 C11 C8 112.5(2) . . ?
F1A C11 C8 117.0(3) . . ?
F1A C11 F3A 108.4(6) . . ?
F1A C11 F2A 102.9(5) . . ?
F3A C11 C8 114.7(4) . . ?
F3A C11 F2A 101.2(6) . . ?
F2A C11 C8 110.9(3) . . ?
O1 C12 O2 122.63(16) . . ?
O1 C12 C3 123.84(16) . . ?
O2 C12 C3 113.50(14) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C4 110.86(13) . . ?
O4 C14 O3 125.27(15) . . ?
O4 C14 C4 123.83(14) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N2 121.74(14) . . ?
C17 C16 C21 119.20(16) . . ?
C21 C16 N2 119.06(14) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.10(16) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.17(17) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C22 120.12(19) . . ?
C20 C19 C18 119.98(17) . . ?
C20 C19 C22 119.89(19) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.01(16) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.50(17) . . ?
C20 C21 H21 119.8 . . ?
F4 C22 F5 103.9(4) . . ?
F4 C22 F6 108.8(4) . . ?
F4 C22 C19 116.0(3) . . ?
F5 C22 C19 112.1(2) . . ?
F6 C22 F5 100.5(3) . . ?
F6 C22 C19 114.1(3) . . ?
F5A C22 C19 111.4(4) . . ?
F5A C22 F4A 99.8(5) . . ?
F4A C22 C19 108.6(3) . . ?
F6A C22 C19 115.1(4) . . ?
F6A C22 F5A 116.8(7) . . ?
F6A C22 F4A 103.3(7) . . ?

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 C2 C3 C4 4.9(2) . . . . ?
N1 C2 C3 C12 -173.11(14) . . . . ?
N1 C5 C6 C7 178.18(14) . . . . ?
N1 C5 C10 C9 -178.28(16) . . . . ?
N2 C4 C14 O3 -124.60(15) . . . . ?
N2 C4 C14 O4 53.5(2) . . . . ?
N2 C16 C17 C18 -178.40(15) . . . . ?
N2 C16 C21 C20 -179.77(15) . . . . ?
C1 N1 C2 C3 -41.08(19) . . . . ?
C1 N1 C5 C6 2.1(2) . . . . ?
C1 N1 C5 C10 -176.43(15) . . . . ?
C1 N2 C4 C3 10.4(2) . . . . ?
C1 N2 C4 C14 -164.77(13) . . . . ?
C1 N2 C16 C17 -133.52(16) . . . . ?
C1 N2 C16 C21 45.9(2) . . . . ?
C2 N1 C1 N2 64.25(17) . . . . ?
C2 N1 C5 C6 -140.77(16) . . . . ?
C2 N1 C5 C10 40.7(2) . . . . ?
C2 C3 C4 N2 11.0(2) . . . . ?
C2 C3 C4 C14 -174.17(15) . . . . ?
C2 C3 C12 O1 26.0(3) . . . . ?
C2 C3 C12 O2 -152.24(15) . . . . ?
C3 C4 C14 O3 60.3(2) . . . . ?
C3 C4 C14 O4 -121.69(19) . . . . ?
C4 N2 C1 N1 -48.05(18) . . . . ?
C4 N2 C16 C17 29.3(2) . . . . ?
C4 N2 C16 C21 -151.27(15) . . . . ?
C4 C3 C12 O1 -152.01(19) . . . . ?
C4 C3 C12 O2 29.8(2) . . . . ?
C5 N1 C1 N2 -81.55(18) . . . . ?
C5 N1 C2 C3 104.95(17) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C5 C10 C9 3.1(3) . . . . ?
C6 C7 C8 C9 2.2(3) . . . . ?
C6 C7 C8 C11 -176.20(18) . . . . ?
C7 C8 C9 C10 -2.4(3) . . . . ?
C7 C8 C11 F1 107.4(5) . . . . ?
C7 C8 C11 F2 -17.1(5) . . . . ?
C7 C8 C11 F3 -135.5(4) . . . . ?
C7 C8 C11 F1A 163.5(8) . . . . ?
C7 C8 C11 F3A -68.0(9) . . . . ?
C7 C8 C11 F2A 45.9(7) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C9 C8 C11 F1 -71.0(6) . . . . ?
C9 C8 C11 F2 164.5(5) . . . . ?
C9 C8 C11 F3 46.1(4) . . . . ?
C9 C8 C11 F1A -14.9(8) . . . . ?
C9 C8 C11 F3A 113.6(8) . . . . ?
C9 C8 C11 F2A -132.5(6) . . . . ?
C10 C5 C6 C7 -3.3(2) . . . . ?
C11 C8 C9 C10 176.03(19) . . . . ?
C12 C3 C4 N2 -171.18(14) . . . . ?
C12 C3 C4 C14 3.7(2) . . . . ?
C13 O2 C12 O1 8.8(3) . . . . ?
C13 O2 C12 C3 -173.00(18) . . . . ?
C15 O3 C14 O4 1.5(3) . . . . ?
C15 O3 C14 C4 179.53(19) . . . . ?
C16 N2 C1 N1 116.39(16) . . . . ?
C16 N2 C4 C3 -153.51(15) . . . . ?
C16 N2 C4 C14 31.3(2) . . . . ?
C16 C17 C18 C19 -2.2(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C17 C18 C19 C22 179.44(19) . . . . ?
C18 C19 C20 C21 1.5(3) . . . . ?
C18 C19 C22 F4 152.9(5) . . . . ?
C18 C19 C22 F5 33.8(4) . . . . ?
C18 C19 C22 F6 -79.5(5) . . . . ?
C18 C19 C22 F5A 106.7(6) . . . . ?
C18 C19 C22 F4A -144.4(6) . . . . ?
C18 C19 C22 F6A -29.1(9) . . . . ?
C19 C20 C21 C16 -1.5(3) . . . . ?
C20 C19 C22 F4 -28.0(6) . . . . ?
C20 C19 C22 F5 -147.1(3) . . . . ?
C20 C19 C22 F6 99.5(4) . . . . ?
C20 C19 C22 F5A -74.2(7) . . . . ?
C20 C19 C22 F4A 34.7(6) . . . . ?
C20 C19 C22 F6A 149.9(9) . . . . ?
C21 C16 C17 C18 2.1(2) . . . . ?
C22 C19 C20 C21 -177.59(19) . . . . ?

_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_zhu6cult
_database_code_depnum_ccdc_archive 'CCDC 2353615'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-01-09
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        5a
_chemical_formula_moiety         'C20 H20 N2 O4'
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38
_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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.4654(6)
_cell_length_b                   8.6484(6)
_cell_length_c                   12.7988(8)
_cell_angle_alpha                82.483(6)
_cell_angle_beta                 74.044(6)
_cell_angle_gamma                76.626(7)
_cell_volume                     874.24(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3597
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4310
_cell_measurement_theta_min      5.7870
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0104
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5049
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         75.43
_diffrn_reflns_theta_min         5.80
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9800
_diffrn_measured_fraction_theta_max 0.9451
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -96.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  125.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
  4 omega   80.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega   33.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   31.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega   68.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega  100.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -90.0000 77
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1304283000
_diffrn_orient_matrix_UB_12      0.0218412000
_diffrn_orient_matrix_UB_13      0.1106200000
_diffrn_orient_matrix_UB_21      -0.1362601000
_diffrn_orient_matrix_UB_22      -0.0240376000
_diffrn_orient_matrix_UB_23      -0.0515107000
_diffrn_orient_matrix_UB_31      0.0426274000
_diffrn_orient_matrix_UB_32      -0.1806766000
_diffrn_orient_matrix_UB_33      0.0293921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3264
_reflns_number_total             3421
_reflns_odcompleteness_completeness 98.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65298(10) 0.77352(10) 0.44179(6) 0.02092(18) Uani 1 1 d . . .
O2 O 0.77029(9) 0.83412(9) 0.26493(6) 0.01875(18) Uani 1 1 d . . .
O3 O 0.42806(10) 1.00502(9) 0.28191(7) 0.02259(19) Uani 1 1 d . . .
O4 O 0.33802(11) 0.94523(9) 0.14482(7) 0.02464(19) Uani 1 1 d . . .
N1 N 0.45698(11) 0.46018(10) 0.21156(7) 0.01530(19) Uani 1 1 d . . .
C2 C 0.47683(13) 0.42165(12) 0.32239(8) 0.0157(2) Uani 1 1 d . . .
H2A H 0.5185 0.3055 0.3337 0.019 Uiso 1 1 calc R . .
H2B H 0.3667 0.4511 0.3752 0.019 Uiso 1 1 calc R . .
N3 N 0.59632(11) 0.50855(10) 0.34139(7) 0.01493(19) Uani 1 1 d . . .
C4 C 0.57232(13) 0.66741(12) 0.30570(8) 0.0148(2) Uani 1 1 d . . .
C5 C 0.45953(13) 0.73335(12) 0.24646(8) 0.0159(2) Uani 1 1 d . . .
C6 C 0.37756(13) 0.62874(12) 0.20065(9) 0.0168(2) Uani 1 1 d . . .
H6A H 0.2571 0.6435 0.2395 0.020 Uiso 1 1 calc R . .
H6B H 0.3854 0.6620 0.1227 0.020 Uiso 1 1 calc R . .
C11 C 0.60788(13) 0.40744(12) 0.13032(8) 0.0155(2) Uani 1 1 d . . .
C12 C 0.68820(14) 0.51097(13) 0.05170(9) 0.0185(2) Uani 1 1 d . . .
H12 H 0.6428 0.6223 0.0509 0.022 Uiso 1 1 calc R . .
C13 C 0.83443(14) 0.45213(14) -0.02558(9) 0.0214(2) Uani 1 1 d . . .
H13 H 0.8877 0.5238 -0.0789 0.026 Uiso 1 1 calc R . .
C14 C 0.90319(14) 0.29066(15) -0.02576(9) 0.0231(2) Uani 1 1 d . . .
H14 H 1.0038 0.2512 -0.0781 0.028 Uiso 1 1 calc R . .
C15 C 0.82266(15) 0.18729(14) 0.05175(10) 0.0235(2) Uani 1 1 d . . .
H15 H 0.8683 0.0761 0.0519 0.028 Uiso 1 1 calc R . .
C16 C 0.67638(14) 0.24409(13) 0.12910(9) 0.0196(2) Uani 1 1 d . . .
H16 H 0.6226 0.1717 0.1814 0.024 Uiso 1 1 calc R . .
C21 C 0.74765(13) 0.42216(12) 0.36664(8) 0.0151(2) Uani 1 1 d . . .
C22 C 0.73922(13) 0.30136(13) 0.45051(8) 0.0171(2) Uani 1 1 d . . .
H22 H 0.6338 0.2776 0.4897 0.020 Uiso 1 1 calc R . .
C23 C 0.88578(15) 0.21594(13) 0.47648(9) 0.0209(2) Uani 1 1 d . . .
H23 H 0.8799 0.1332 0.5332 0.025 Uiso 1 1 calc R . .
C24 C 1.04076(14) 0.25025(14) 0.42036(10) 0.0235(2) Uani 1 1 d . . .
H24 H 1.1402 0.1928 0.4393 0.028 Uiso 1 1 calc R . .
C25 C 1.04860(14) 0.36943(14) 0.33626(10) 0.0224(2) Uani 1 1 d . . .
H25 H 1.1542 0.3931 0.2973 0.027 Uiso 1 1 calc R . .
C26 C 0.90307(13) 0.45463(13) 0.30857(9) 0.0186(2) Uani 1 1 d . . .
H26 H 0.9097 0.5348 0.2501 0.022 Uiso 1 1 calc R . .
C30 C 0.66695(13) 0.76498(12) 0.34681(9) 0.0161(2) Uani 1 1 d . . .
C31 C 0.86627(16) 0.92622(15) 0.30018(10) 0.0277(3) Uani 1 1 d . . .
H31A H 0.9423 0.9691 0.2364 0.042 Uiso 1 1 calc R . .
H31B H 0.9319 0.8577 0.3472 0.042 Uiso 1 1 calc R . .
H31C H 0.7897 1.0143 0.3408 0.042 Uiso 1 1 calc R . .
C40 C 0.41060(13) 0.90696(13) 0.22884(9) 0.0174(2) Uani 1 1 d . . .
C41 C 0.28076(19) 1.11270(14) 0.11975(12) 0.0329(3) Uani 1 1 d . . .
H41A H 0.2449 1.1278 0.0519 0.049 Uiso 1 1 calc R . .
H41B H 0.3724 1.1686 0.1111 0.049 Uiso 1 1 calc R . .
H41C H 0.1860 1.1557 0.1792 0.049 Uiso 1 1 calc R . .


_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 C30 1.1990(13) . ?
O2 C30 1.3399(13) . ?
O2 C31 1.4468(13) . ?
O3 C40 1.2109(14) . ?
O4 C40 1.3489(14) . ?
O4 C41 1.4405(14) . ?
N1 C2 1.4604(13) . ?
N1 C6 1.4634(13) . ?
N1 C11 1.4301(14) . ?
C2 N3 1.4771(13) . ?
N3 C4 1.3767(13) . ?
N3 C21 1.4232(13) . ?
C4 C5 1.3582(15) . ?
C4 C30 1.5137(14) . ?
C5 C6 1.5156(14) . ?
C5 C40 1.4669(14) . ?
C11 C12 1.3951(15) . ?
C11 C16 1.3979(15) . ?
C12 C13 1.3916(16) . ?
C13 C14 1.3831(17) . ?
C14 C15 1.3879(17) . ?
C15 C16 1.3880(16) . ?
C21 C22 1.3956(15) . ?
C21 C26 1.3932(15) . ?
C22 C23 1.3907(15) . ?
C23 C24 1.3899(17) . ?
C24 C25 1.3883(17) . ?
C25 C26 1.3922(16) . ?

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
C30 O2 C31 113.99(8) . . ?
C40 O4 C41 116.24(9) . . ?
C2 N1 C6 108.56(8) . . ?
C11 N1 C2 112.92(8) . . ?
C11 N1 C6 116.19(8) . . ?
N1 C2 N3 110.35(8) . . ?
C4 N3 C2 115.03(8) . . ?
C4 N3 C21 123.04(9) . . ?
C21 N3 C2 119.79(8) . . ?
N3 C4 C30 115.14(9) . . ?
C5 C4 N3 121.81(9) . . ?
C5 C4 C30 122.77(9) . . ?
C4 C5 C6 120.48(9) . . ?
C4 C5 C40 120.67(10) . . ?
C40 C5 C6 118.82(9) . . ?
N1 C6 C5 111.81(8) . . ?
C12 C11 N1 123.11(9) . . ?
C12 C11 C16 118.69(10) . . ?
C16 C11 N1 118.20(9) . . ?
C13 C12 C11 120.37(10) . . ?
C14 C13 C12 120.85(10) . . ?
C13 C14 C15 118.89(10) . . ?
C14 C15 C16 120.94(11) . . ?
C15 C16 C11 120.26(10) . . ?
C22 C21 N3 118.95(9) . . ?
C26 C21 N3 121.33(9) . . ?
C26 C21 C22 119.72(10) . . ?
C23 C22 C21 119.74(10) . . ?
C24 C23 C22 120.74(10) . . ?
C25 C24 C23 119.27(11) . . ?
C24 C25 C26 120.58(10) . . ?
C25 C26 C21 119.92(10) . . ?
O1 C30 O2 125.08(10) . . ?
O1 C30 C4 122.97(10) . . ?
O2 C30 C4 111.91(9) . . ?
O3 C40 O4 123.36(10) . . ?
O3 C40 C5 126.27(10) . . ?
O4 C40 C5 110.36(9) . . ?

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 C2 N3 C4 45.73(11) . . . . ?
N1 C2 N3 C21 -118.14(10) . . . . ?
N1 C11 C12 C13 -179.68(10) . . . . ?
N1 C11 C16 C15 179.97(10) . . . . ?
C2 N1 C6 C5 46.93(11) . . . . ?
C2 N1 C11 C12 -119.20(11) . . . . ?
C2 N1 C11 C16 61.68(12) . . . . ?
C2 N3 C4 C5 -7.23(14) . . . . ?
C2 N3 C4 C30 166.82(8) . . . . ?
C2 N3 C21 C22 -51.12(13) . . . . ?
C2 N3 C21 C26 128.08(10) . . . . ?
N3 C4 C5 C6 -10.74(15) . . . . ?
N3 C4 C5 C40 167.16(9) . . . . ?
N3 C4 C30 O1 -56.52(14) . . . . ?
N3 C4 C30 O2 121.29(10) . . . . ?
N3 C21 C22 C23 -179.85(9) . . . . ?
N3 C21 C26 C25 179.13(10) . . . . ?
C4 N3 C21 C22 146.36(10) . . . . ?
C4 N3 C21 C26 -34.44(15) . . . . ?
C4 C5 C6 N1 -10.27(14) . . . . ?
C4 C5 C40 O3 -18.89(17) . . . . ?
C4 C5 C40 O4 162.46(10) . . . . ?
C5 C4 C30 O1 117.46(12) . . . . ?
C5 C4 C30 O2 -64.72(13) . . . . ?
C6 N1 C2 N3 -65.59(10) . . . . ?
C6 N1 C11 C12 7.19(14) . . . . ?
C6 N1 C11 C16 -171.93(9) . . . . ?
C6 C5 C40 O3 159.05(11) . . . . ?
C6 C5 C40 O4 -19.60(13) . . . . ?
C11 N1 C2 N3 64.77(11) . . . . ?
C11 N1 C6 C5 -81.62(11) . . . . ?
C11 C12 C13 C14 -0.27(16) . . . . ?
C12 C11 C16 C15 0.82(16) . . . . ?
C12 C13 C14 C15 0.84(17) . . . . ?
C13 C14 C15 C16 -0.59(17) . . . . ?
C14 C15 C16 C11 -0.24(17) . . . . ?
C16 C11 C12 C13 -0.57(16) . . . . ?
C21 N3 C4 C5 156.05(10) . . . . ?
C21 N3 C4 C30 -29.90(13) . . . . ?
C21 C22 C23 C24 0.48(17) . . . . ?
C22 C21 C26 C25 -1.68(16) . . . . ?
C22 C23 C24 C25 -1.13(17) . . . . ?
C23 C24 C25 C26 0.38(18) . . . . ?
C24 C25 C26 C21 1.03(17) . . . . ?
C26 C21 C22 C23 0.93(16) . . . . ?
C30 C4 C5 C6 175.66(9) . . . . ?
C30 C4 C5 C40 -6.43(15) . . . . ?
C31 O2 C30 O1 -1.04(15) . . . . ?
C31 O2 C30 C4 -178.80(9) . . . . ?
C40 C5 C6 N1 171.78(9) . . . . ?
C41 O4 C40 O3 0.18(16) . . . . ?
C41 O4 C40 C5 178.88(10) . . . . ?

####################################################################### 
# 
# 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_240423hsz4_0m
_database_code_depnum_ccdc_archive 'CCDC 2353765'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-04-25
_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         'C20 H18 Cl2 N2 O4'
_chemical_formula_sum            'C20 H18 Cl2 N2 O4'
_chemical_formula_weight         421.26
_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'
Cl Cl 0.3639 0.7018 '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                   14.5906(2)
_cell_length_b                   11.6185(2)
_cell_length_c                   24.5111(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.3010(10)
_cell_angle_gamma                90
_cell_volume                     3967.15(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      68.184
_cell_measurement_theta_min      3.172
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.197
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1092 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.6848.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            38290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.368
_diffrn_reflns_theta_min         3.172
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6565
_reflns_number_total             7457
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00138(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         7457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.044
_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)+(0.0643P)²+0.5410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7604(8)
 0.2396(8)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C29(H29A,H29B), C39(H39A,H39B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C22(H22), C28(H28), C30(H30), C32(H32), C36(H36), C38(H38), C40(H40),
 C3(H3), C9(H9), C13(H13), C19(H19), C27(H27), C31(H31), C33(H33), C35(H35)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C20(H20A,H20B,H20C), C7(H7A,H7B,H7C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.91449(6) 0.48591(9) 0.43035(3) 0.0937(3) Uani 1 1 d . . . . .
Cl4 Cl 0.95050(8) 0.66619(10) 0.07858(5) 0.1048(3) Uani 1 1 d . . . . .
O1 O 0.40509(12) 0.62628(15) 0.04724(6) 0.0518(4) Uani 1 1 d . . . . .
O4 O 0.59154(11) 0.71585(13) 0.22412(7) 0.0454(3) Uani 1 1 d . . . . .
O6 O 0.49764(13) 0.59847(15) 0.25679(7) 0.0570(4) Uani 1 1 d . . . . .
O8 O 0.40782(11) 0.69478(14) 0.13324(6) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.62177(13) 0.44648(15) 0.20490(7) 0.0414(4) Uani 1 1 d . . . . .
N4 N 0.62234(14) 0.39771(16) 0.10898(7) 0.0439(4) Uani 1 1 d . . . . .
C1 C 0.7622(2) 0.6306(2) 0.06568(11) 0.0620(7) Uani 1 1 d . . . . .
H1 H 0.751885 0.698963 0.044980 0.074 Uiso 1 1 calc R U . . .
C4 C 0.5836(2) 0.8030(2) 0.26468(12) 0.0648(7) Uani 1 1 d . . . . .
H4A H 0.517034 0.818069 0.260152 0.097 Uiso 1 1 calc R U . . .
H4B H 0.614223 0.872414 0.257967 0.097 Uiso 1 1 calc R U . . .
H4C H 0.614188 0.776236 0.302818 0.097 Uiso 1 1 calc R U . . .
C6 C 0.50687(15) 0.53594(18) 0.12591(9) 0.0409(4) Uani 1 1 d . . . . .
C8 C 0.52585(17) 0.4459(2) 0.08620(9) 0.0491(5) Uani 1 1 d . . . . .
H8A H 0.478810 0.384704 0.081099 0.059 Uiso 1 1 calc R U . . .
H8B H 0.519110 0.480166 0.049126 0.059 Uiso 1 1 calc R U . . .
C10 C 0.55781(14) 0.53276(18) 0.18210(8) 0.0374(4) Uani 1 1 d . . . . .
C12 C 0.8541(2) 0.5887(3) 0.08824(12) 0.0643(7) Uani 1 1 d . . . . .
C14 C 0.43646(15) 0.62617(19) 0.10463(9) 0.0409(4) Uani 1 1 d . . . . .
C16 C 0.63208(18) 0.35390(19) 0.16561(9) 0.0462(5) Uani 1 1 d . . . . .
H16A H 0.694535 0.317974 0.180688 0.055 Uiso 1 1 calc R U . . .
H16B H 0.583541 0.295570 0.163380 0.055 Uiso 1 1 calc R U . . .
C18 C 0.69262(14) 0.45715(18) 0.25934(8) 0.0386(4) Uani 1 1 d . . . . .
C20 C 0.3304(2) 0.7078(3) 0.02203(11) 0.0687(8) Uani 1 1 d . . . . .
H20A H 0.312028 0.700817 -0.018827 0.103 Uiso 1 1 calc R U . . .
H20B H 0.353445 0.784384 0.032860 0.103 Uiso 1 1 calc R U . . .
H20C H 0.275851 0.692740 0.035210 0.103 Uiso 1 1 calc R U . . .
C22 C 0.83035(17) 0.5509(2) 0.32186(10) 0.0491(5) Uani 1 1 d . . . . .
H22 H 0.877067 0.608034 0.328627 0.059 Uiso 1 1 calc R U . . .
C24 C 0.54377(15) 0.61917(18) 0.22523(8) 0.0395(4) Uani 1 1 d . . . . .
C26 C 0.82839(17) 0.4745(2) 0.36388(9) 0.0504(5) Uani 1 1 d . . . . .
C28 C 0.76185(16) 0.54212(19) 0.26920(9) 0.0450(5) Uani 1 1 d . . . . .
H28 H 0.762343 0.593635 0.240250 0.054 Uiso 1 1 calc R U . . .
C30 C 0.79334(18) 0.4265(2) 0.12512(10) 0.0540(6) Uani 1 1 d . . . . .
H30 H 0.804556 0.356945 0.144732 0.065 Uiso 1 1 calc R U . . .
C32 C 0.76168(18) 0.3869(2) 0.35446(11) 0.0587(6) Uani 1 1 d . . . . .
H32 H 0.762831 0.334248 0.383221 0.070 Uiso 1 1 calc R U . . .
C34 C 0.69927(16) 0.46644(18) 0.10338(8) 0.0422(5) Uani 1 1 d . . . . .
C36 C 0.6858(2) 0.5711(2) 0.07391(10) 0.0536(6) Uani 1 1 d . . . . .
H36 H 0.624188 0.600953 0.059601 0.064 Uiso 1 1 calc R U . . .
C38 C 0.8698(2) 0.4876(3) 0.11822(12) 0.0637(7) Uani 1 1 d . . . . .
H38 H 0.932049 0.460376 0.133892 0.076 Uiso 1 1 calc R U . . .
C40 C 0.69333(17) 0.3784(2) 0.30197(10) 0.0497(5) Uani 1 1 d . . . . .
H40 H 0.647756 0.319970 0.295136 0.060 Uiso 1 1 calc R U . . .
Cl2 Cl 0.22446(8) 0.45345(8) 0.07173(3) 0.0942(3) Uani 1 1 d . . . . .
Cl3 Cl 0.64605(7) 0.62875(11) 0.42642(5) 0.1102(3) Uani 1 1 d . . . . .
O2 O 0.11920(10) 0.72441(13) 0.27377(6) 0.0435(3) Uani 1 1 d . . . . .
O3 O 0.11856(12) 0.66644(15) 0.45374(6) 0.0522(4) Uani 1 1 d . . . . .
O5 O 0.03073(11) 0.71573(14) 0.36515(7) 0.0502(4) Uani 1 1 d . . . . .
O7 O -0.00470(12) 0.60125(15) 0.24646(7) 0.0556(4) Uani 1 1 d . . . . .
N2 N 0.17198(14) 0.45572(15) 0.30196(7) 0.0457(4) Uani 1 1 d . . . . .
N3 N 0.26609(15) 0.41072(17) 0.39840(8) 0.0500(5) Uani 1 1 d . . . . .
C2 C 0.5336(2) 0.5655(3) 0.41693(13) 0.0673(7) Uani 1 1 d . . . . .
C3 C 0.23751(18) 0.5422(2) 0.23077(10) 0.0510(5) Uani 1 1 d . . . . .
H3 H 0.265166 0.600257 0.256557 0.061 Uiso 1 1 calc R U . . .
C5 C 0.18532(15) 0.45650(18) 0.24657(9) 0.0408(4) Uani 1 1 d . . . . .
C7 C 0.0691(2) 0.7545(3) 0.47545(11) 0.0642(7) Uani 1 1 d . . . . .
H7A H 0.075849 0.827044 0.458311 0.096 Uiso 1 1 calc R U . . .
H7B H 0.096178 0.759889 0.516167 0.096 Uiso 1 1 calc R U . . .
H7C H 0.002243 0.735143 0.466328 0.096 Uiso 1 1 calc R U . . .
C9 C 0.3772(2) 0.5720(3) 0.42801(15) 0.0735(8) Uani 1 1 d . . . . .
H9 H 0.331305 0.612092 0.439847 0.088 Uiso 1 1 calc R U . . .
C11 C 0.35445(18) 0.46674(19) 0.40312(9) 0.0477(5) Uani 1 1 d . . . . .
C13 C 0.2489(2) 0.5425(2) 0.17695(12) 0.0578(6) Uani 1 1 d . . . . .
H13 H 0.283495 0.600974 0.166159 0.069 Uiso 1 1 calc R U . . .
C15 C 0.07319(15) 0.62726(18) 0.27684(9) 0.0400(4) Uani 1 1 d . . . . .
C17 C 0.20884(19) 0.4556(2) 0.13930(10) 0.0532(6) Uani 1 1 d . . . . .
C19 C 0.5118(2) 0.4613(3) 0.39004(14) 0.0813(9) Uani 1 1 d . . . . .
H19 H 0.556469 0.424236 0.375881 0.098 Uiso 1 1 calc R U . . .
C21 C 0.0678(2) 0.8057(2) 0.23086(12) 0.0636(7) Uani 1 1 d . . . . .
H21A H 0.062447 0.775633 0.193553 0.095 Uiso 1 1 calc R U . . .
H21B H 0.102037 0.877356 0.236050 0.095 Uiso 1 1 calc R U . . .
H21C H 0.004819 0.817957 0.234493 0.095 Uiso 1 1 calc R U . . .
C23 C 0.13259(15) 0.54687(18) 0.32229(9) 0.0395(4) Uani 1 1 d . . . . .
C25 C 0.09003(15) 0.65342(19) 0.39659(9) 0.0411(5) Uani 1 1 d . . . . .
C27 C 0.4235(2) 0.4112(3) 0.38398(13) 0.0718(8) Uani 1 1 d . . . . .
H27 H 0.410020 0.339299 0.366831 0.086 Uiso 1 1 calc R U . . .
C29 C 0.2158(2) 0.3640(2) 0.34298(10) 0.0533(6) Uani 1 1 d . . . . .
H29A H 0.166117 0.311859 0.346709 0.064 Uiso 1 1 calc R U . . .
H29B H 0.260365 0.320403 0.328563 0.064 Uiso 1 1 calc R U . . .
C31 C 0.15869(19) 0.3686(2) 0.15490(11) 0.0569(6) Uani 1 1 d . . . . .
H31 H 0.132567 0.309717 0.129299 0.068 Uiso 1 1 calc R U . . .
C33 C 0.14691(18) 0.3684(2) 0.20873(10) 0.0514(5) Uani 1 1 d . . . . .
H33 H 0.113180 0.309076 0.219546 0.062 Uiso 1 1 calc R U . . .
C35 C 0.4665(3) 0.6207(3) 0.43608(16) 0.0818(9) Uani 1 1 d . . . . .
H35 H 0.481005 0.691172 0.454608 0.098 Uiso 1 1 calc R U . . .
C37 C 0.13974(16) 0.55890(19) 0.37842(9) 0.0428(5) Uani 1 1 d . . . . .
C39 C 0.19711(18) 0.4718(2) 0.42103(10) 0.0522(6) Uani 1 1 d . . . . .
H39A H 0.231345 0.510987 0.456137 0.063 Uiso 1 1 calc R U . . .
H39B H 0.153703 0.416706 0.429908 0.063 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 C26 1.741(2) . ?
Cl4 C12 1.745(3) . ?
O1 C14 1.344(2) . ?
O1 C20 1.438(3) . ?
O4 C4 1.448(3) . ?
O4 C24 1.327(3) . ?
O6 C24 1.191(3) . ?
O8 C14 1.215(3) . ?
N1 C10 1.370(3) . ?
N1 C16 1.481(3) . ?
N1 C18 1.430(3) . ?
N4 C8 1.463(3) . ?
N4 C16 1.445(3) . ?
N4 C34 1.417(3) . ?
C1 H1 0.9300 . ?
C1 C12 1.378(4) . ?
C1 C36 1.377(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C8 1.510(3) . ?
C6 C10 1.357(3) . ?
C6 C14 1.452(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C24 1.515(3) . ?
C12 C38 1.367(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C28 1.381(3) . ?
C18 C40 1.387(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C26 1.367(3) . ?
C22 C28 1.381(3) . ?
C26 C32 1.379(3) . ?
C28 H28 0.9300 . ?
C30 H30 0.9300 . ?
C30 C34 1.396(3) . ?
C30 C38 1.375(4) . ?
C32 H32 0.9300 . ?
C32 C40 1.377(3) . ?
C34 C36 1.398(3) . ?
C36 H36 0.9300 . ?
C38 H38 0.9300 . ?
C40 H40 0.9300 . ?
Cl2 C17 1.738(2) . ?
Cl3 C2 1.749(3) . ?
O2 C15 1.327(3) . ?
O2 C21 1.446(3) . ?
O3 C7 1.442(3) . ?
O3 C25 1.346(3) . ?
O5 C25 1.212(3) . ?
O7 C15 1.197(3) . ?
N2 C5 1.428(3) . ?
N2 C23 1.368(3) . ?
N2 C29 1.474(3) . ?
N3 C11 1.418(3) . ?
N3 C29 1.444(3) . ?
N3 C39 1.469(3) . ?
C2 C19 1.370(5) . ?
C2 C35 1.365(4) . ?
C3 H3 0.9300 . ?
C3 C5 1.378(3) . ?
C3 C13 1.378(3) . ?
C5 C33 1.383(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C11 1.363(4) . ?
C9 C35 1.379(5) . ?
C11 C27 1.390(4) . ?
C13 H13 0.9300 . ?
C13 C17 1.376(4) . ?
C15 C23 1.513(3) . ?
C17 C31 1.367(4) . ?
C19 H19 0.9300 . ?
C19 C27 1.380(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 C37 1.356(3) . ?
C25 C37 1.457(3) . ?
C27 H27 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C31 H31 0.9300 . ?
C31 C33 1.380(3) . ?
C33 H33 0.9300 . ?
C35 H35 0.9300 . ?
C37 C39 1.515(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 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
C14 O1 C20 115.43(18) . . ?
C24 O4 C4 115.35(18) . . ?
C10 N1 C16 117.04(17) . . ?
C10 N1 C18 122.20(17) . . ?
C18 N1 C16 119.00(17) . . ?
C16 N4 C8 108.06(18) . . ?
C34 N4 C8 116.59(18) . . ?
C34 N4 C16 115.91(18) . . ?
C12 C1 H1 120.1 . . ?
C36 C1 H1 120.1 . . ?
C36 C1 C12 119.8(2) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C6 C8 119.03(19) . . ?
C10 C6 C14 119.99(19) . . ?
C14 C6 C8 120.97(18) . . ?
N4 C8 C6 111.06(17) . . ?
N4 C8 H8A 109.4 . . ?
N4 C8 H8B 109.4 . . ?
C6 C8 H8A 109.4 . . ?
C6 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C10 C24 114.65(17) . . ?
C6 C10 N1 122.34(19) . . ?
C6 C10 C24 122.89(19) . . ?
C1 C12 Cl4 119.3(2) . . ?
C38 C12 Cl4 120.2(2) . . ?
C38 C12 C1 120.5(3) . . ?
O1 C14 C6 111.18(18) . . ?
O8 C14 O1 122.3(2) . . ?
O8 C14 C6 126.47(19) . . ?
N1 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
N4 C16 N1 111.64(17) . . ?
N4 C16 H16A 109.3 . . ?
N4 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C28 C18 N1 120.90(18) . . ?
C28 C18 C40 119.90(19) . . ?
C40 C18 N1 119.17(19) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C22 H22 120.5 . . ?
C26 C22 C28 119.0(2) . . ?
C28 C22 H22 120.5 . . ?
O4 C24 C10 111.46(17) . . ?
O6 C24 O4 125.9(2) . . ?
O6 C24 C10 122.62(19) . . ?
C22 C26 Cl1 118.97(18) . . ?
C22 C26 C32 121.7(2) . . ?
C32 C26 Cl1 119.34(18) . . ?
C18 C28 C22 120.3(2) . . ?
C18 C28 H28 119.8 . . ?
C22 C28 H28 119.8 . . ?
C34 C30 H30 119.2 . . ?
C38 C30 H30 119.2 . . ?
C38 C30 C34 121.6(2) . . ?
C26 C32 H32 120.4 . . ?
C40 C32 C26 119.2(2) . . ?
C40 C32 H32 120.4 . . ?
C30 C34 N4 119.6(2) . . ?
C30 C34 C36 117.2(2) . . ?
C36 C34 N4 123.1(2) . . ?
C1 C36 C34 121.2(2) . . ?
C1 C36 H36 119.4 . . ?
C34 C36 H36 119.4 . . ?
C12 C38 C30 119.8(3) . . ?
C12 C38 H38 120.1 . . ?
C30 C38 H38 120.1 . . ?
C18 C40 H40 120.1 . . ?
C32 C40 C18 119.8(2) . . ?
C32 C40 H40 120.1 . . ?
C15 O2 C21 115.79(18) . . ?
C25 O3 C7 115.47(18) . . ?
C5 N2 C29 119.94(18) . . ?
C23 N2 C5 122.17(17) . . ?
C23 N2 C29 117.08(17) . . ?
C11 N3 C29 116.4(2) . . ?
C11 N3 C39 117.11(19) . . ?
C29 N3 C39 108.9(2) . . ?
C19 C2 Cl3 120.7(2) . . ?
C35 C2 Cl3 119.8(3) . . ?
C35 C2 C19 119.5(3) . . ?
C5 C3 H3 119.8 . . ?
C5 C3 C13 120.3(2) . . ?
C13 C3 H3 119.8 . . ?
C3 C5 N2 120.99(19) . . ?
C3 C5 C33 119.6(2) . . ?
C33 C5 N2 119.36(19) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C9 H9 119.1 . . ?
C11 C9 C35 121.7(3) . . ?
C35 C9 H9 119.1 . . ?
C9 C11 N3 122.9(2) . . ?
C9 C11 C27 117.6(3) . . ?
C27 C11 N3 119.5(2) . . ?
C3 C13 H13 120.3 . . ?
C17 C13 C3 119.5(2) . . ?
C17 C13 H13 120.3 . . ?
O2 C15 C23 112.22(17) . . ?
O7 C15 O2 125.6(2) . . ?
O7 C15 C23 122.1(2) . . ?
C13 C17 Cl2 120.0(2) . . ?
C31 C17 Cl2 119.26(19) . . ?
C31 C17 C13 120.8(2) . . ?
C2 C19 H19 120.0 . . ?
C2 C19 C27 120.0(3) . . ?
C27 C19 H19 120.0 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C23 C15 114.86(18) . . ?
C37 C23 N2 122.39(19) . . ?
C37 C23 C15 122.54(19) . . ?
O3 C25 C37 112.02(18) . . ?
O5 C25 O3 122.4(2) . . ?
O5 C25 C37 125.58(19) . . ?
C11 C27 H27 119.5 . . ?
C19 C27 C11 121.0(3) . . ?
C19 C27 H27 119.5 . . ?
N2 C29 H29A 109.3 . . ?
N2 C29 H29B 109.3 . . ?
N3 C29 N2 111.48(18) . . ?
N3 C29 H29A 109.3 . . ?
N3 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C17 C31 H31 120.1 . . ?
C17 C31 C33 119.9(2) . . ?
C33 C31 H31 120.1 . . ?
C5 C33 H33 120.0 . . ?
C31 C33 C5 119.9(2) . . ?
C31 C33 H33 120.0 . . ?
C2 C35 C9 120.1(3) . . ?
C2 C35 H35 120.0 . . ?
C9 C35 H35 120.0 . . ?
C23 C37 C25 119.53(19) . . ?
C23 C37 C39 119.4(2) . . ?
C25 C37 C39 121.04(18) . . ?
N3 C39 C37 111.25(18) . . ?
N3 C39 H39A 109.4 . . ?
N3 C39 H39B 109.4 . . ?
C37 C39 H39A 109.4 . . ?
C37 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?

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
Cl1 C26 C32 C40 179.6(2) . . . . ?
Cl4 C12 C38 C30 -179.3(2) . . . . ?
N1 C10 C24 O4 102.1(2) . . . . ?
N1 C10 C24 O6 -75.7(3) . . . . ?
N1 C18 C28 C22 -179.5(2) . . . . ?
N1 C18 C40 C32 179.4(2) . . . . ?
N4 C34 C36 C1 -174.8(2) . . . . ?
C1 C12 C38 C30 1.1(4) . . . . ?
C4 O4 C24 O6 -1.4(3) . . . . ?
C4 O4 C24 C10 -179.04(19) . . . . ?
C6 C10 C24 O4 -81.9(3) . . . . ?
C6 C10 C24 O6 100.4(3) . . . . ?
C8 N4 C16 N1 -61.9(2) . . . . ?
C8 N4 C34 C30 178.9(2) . . . . ?
C8 N4 C34 C36 -5.0(3) . . . . ?
C8 C6 C10 N1 -4.2(3) . . . . ?
C8 C6 C10 C24 -179.89(19) . . . . ?
C8 C6 C14 O1 -9.1(3) . . . . ?
C8 C6 C14 O8 171.3(2) . . . . ?
C10 N1 C16 N4 35.1(3) . . . . ?
C10 N1 C18 C28 -61.1(3) . . . . ?
C10 N1 C18 C40 121.1(2) . . . . ?
C10 C6 C8 N4 -23.8(3) . . . . ?
C10 C6 C14 O1 169.9(2) . . . . ?
C10 C6 C14 O8 -9.8(3) . . . . ?
C12 C1 C36 C34 -1.9(4) . . . . ?
C14 C6 C8 N4 155.2(2) . . . . ?
C14 C6 C10 N1 176.82(19) . . . . ?
C14 C6 C10 C24 1.1(3) . . . . ?
C16 N1 C10 C6 -1.2(3) . . . . ?
C16 N1 C10 C24 174.81(18) . . . . ?
C16 N1 C18 C28 103.4(2) . . . . ?
C16 N1 C18 C40 -74.4(3) . . . . ?
C16 N4 C8 C6 55.5(2) . . . . ?
C16 N4 C34 C30 49.9(3) . . . . ?
C16 N4 C34 C36 -133.9(2) . . . . ?
C18 N1 C10 C6 163.5(2) . . . . ?
C18 N1 C10 C24 -20.5(3) . . . . ?
C18 N1 C16 N4 -130.2(2) . . . . ?
C20 O1 C14 O8 -4.2(3) . . . . ?
C20 O1 C14 C6 176.1(2) . . . . ?
C22 C26 C32 C40 -2.1(4) . . . . ?
C26 C22 C28 C18 0.0(4) . . . . ?
C26 C32 C40 C18 0.3(4) . . . . ?
C28 C18 C40 C32 1.6(4) . . . . ?
C28 C22 C26 Cl1 -179.77(19) . . . . ?
C28 C22 C26 C32 2.0(4) . . . . ?
C30 C34 C36 C1 1.4(3) . . . . ?
C34 N4 C8 C6 -77.1(2) . . . . ?
C34 N4 C16 N1 71.1(2) . . . . ?
C34 C30 C38 C12 -1.6(4) . . . . ?
C36 C1 C12 Cl4 -178.9(2) . . . . ?
C36 C1 C12 C38 0.7(4) . . . . ?
C38 C30 C34 N4 176.8(2) . . . . ?
C38 C30 C34 C36 0.4(3) . . . . ?
C40 C18 C28 C22 -1.7(3) . . . . ?
Cl2 C17 C31 C33 179.1(2) . . . . ?
Cl3 C2 C19 C27 178.6(3) . . . . ?
Cl3 C2 C35 C9 179.1(3) . . . . ?
O2 C15 C23 N2 -104.1(2) . . . . ?
O2 C15 C23 C37 81.1(3) . . . . ?
O3 C25 C37 C23 -168.2(2) . . . . ?
O3 C25 C37 C39 13.5(3) . . . . ?
O5 C25 C37 C23 10.7(3) . . . . ?
O5 C25 C37 C39 -167.6(2) . . . . ?
O7 C15 C23 N2 73.2(3) . . . . ?
O7 C15 C23 C37 -101.6(3) . . . . ?
N2 C5 C33 C31 179.5(2) . . . . ?
N2 C23 C37 C25 -175.4(2) . . . . ?
N2 C23 C37 C39 2.9(3) . . . . ?
N3 C11 C27 C19 -177.3(3) . . . . ?
C2 C19 C27 C11 2.1(5) . . . . ?
C3 C5 C33 C31 -1.9(4) . . . . ?
C3 C13 C17 Cl2 -178.9(2) . . . . ?
C3 C13 C17 C31 -0.6(4) . . . . ?
C5 N2 C23 C15 20.9(3) . . . . ?
C5 N2 C23 C37 -164.3(2) . . . . ?
C5 N2 C29 N3 131.5(2) . . . . ?
C5 C3 C13 C17 -0.8(4) . . . . ?
C7 O3 C25 O5 4.1(3) . . . . ?
C7 O3 C25 C37 -176.9(2) . . . . ?
C9 C11 C27 C19 0.0(4) . . . . ?
C11 N3 C29 N2 -73.3(3) . . . . ?
C11 N3 C39 C37 82.2(3) . . . . ?
C11 C9 C35 C2 2.7(6) . . . . ?
C13 C3 C5 N2 -179.3(2) . . . . ?
C13 C3 C5 C33 2.1(4) . . . . ?
C13 C17 C31 C33 0.8(4) . . . . ?
C15 C23 C37 C25 -1.0(3) . . . . ?
C15 C23 C37 C39 177.3(2) . . . . ?
C17 C31 C33 C5 0.4(4) . . . . ?
C19 C2 C35 C9 -0.5(5) . . . . ?
C21 O2 C15 O7 2.1(3) . . . . ?
C21 O2 C15 C23 179.31(19) . . . . ?
C23 N2 C5 C3 56.1(3) . . . . ?
C23 N2 C5 C33 -125.3(2) . . . . ?
C23 N2 C29 N3 -38.4(3) . . . . ?
C23 C37 C39 N3 21.3(3) . . . . ?
C25 C37 C39 N3 -160.4(2) . . . . ?
C29 N2 C5 C3 -113.3(2) . . . . ?
C29 N2 C5 C33 65.3(3) . . . . ?
C29 N2 C23 C15 -169.44(19) . . . . ?
C29 N2 C23 C37 5.4(3) . . . . ?
C29 N3 C11 C9 132.1(3) . . . . ?
C29 N3 C11 C27 -50.7(3) . . . . ?
C29 N3 C39 C37 -52.5(3) . . . . ?
C35 C2 C19 C27 -1.9(5) . . . . ?
C35 C9 C11 N3 174.8(3) . . . . ?
C35 C9 C11 C27 -2.4(5) . . . . ?
C39 N3 C11 C9 0.8(3) . . . . ?
C39 N3 C11 C27 178.0(2) . . . . ?
C39 N3 C29 N2 61.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7604(8)
2 0.2396(8)

####################################################################### 
# 
# 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_mo_240423hsz2_0m
_database_code_depnum_ccdc_archive 'CCDC 2353822'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_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         'C20 H18 F2 N2 O4'
_chemical_formula_sum            'C20 H18 F2 N2 O4'
_chemical_formula_weight         388.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7578(2)
_cell_length_b                   9.7459(3)
_cell_length_c                   12.3859(4)
_cell_angle_alpha                96.6910(10)
_cell_angle_beta                 108.3500(10)
_cell_angle_gamma                106.1870(10)
_cell_volume                     939.12(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6462
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      27.980
_cell_measurement_theta_min      2.233
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1596 before and 0.1045 after correction.
The Ratio of minimum to maximum transmission is 0.7526.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19999
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.233
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3314
_reflns_number_total             4626
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0763
_refine_ls_restrained_S_all      1.065
_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)+(0.1566P)²+0.1190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2297
_refine_ls_wR_factor_ref         0.2544
_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:
 C18(H18A,H18B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C11(H11), C3(H3), C7(H7), C15(H15), C2(H2), C9(H9)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1280(2) 0.2522(2) 0.30175(14) 0.0659(5) Uani 1 1 d . . . . .
O4 O -0.10790(19) 0.15029(18) 0.06513(15) 0.0617(4) Uani 1 1 d . . . . .
O5 O -0.0164(2) 0.2925(2) -0.04673(15) 0.0671(5) Uani 1 1 d . . . . .
N1 N 0.3898(2) 0.12870(18) 0.20063(15) 0.0480(4) Uani 1 1 d . . . . .
N2 N 0.4616(2) 0.2516(2) 0.05621(15) 0.0515(4) Uani 1 1 d . . . . .
O3 O 0.0965(2) 0.0128(2) 0.27281(19) 0.0801(6) Uani 1 1 d . . . . .
C1 C 0.2406(2) 0.1615(2) 0.17148(16) 0.0446(4) Uani 1 1 d . . . . .
C4 C 0.0047(3) 0.2112(2) 0.03270(17) 0.0494(5) Uani 1 1 d . . . . .
F2 F 0.6481(3) 0.3969(3) 0.59942(19) 0.1254(8) Uani 1 1 d . . . . .
C6 C 0.5742(3) 0.3859(2) 0.13384(17) 0.0484(5) Uani 1 1 d . . . . .
C8 C 0.4973(2) 0.1504(2) 0.31852(18) 0.0471(4) Uani 1 1 d . . . . .
C10 C 0.1447(3) 0.1311(2) 0.25316(19) 0.0536(5) Uani 1 1 d . . . . .
F12 F 0.5874(4) 0.7385(2) 0.2644(3) 0.1321(9) Uani 1 1 d . . . . .
C14 C 0.1789(2) 0.2055(2) 0.07234(17) 0.0477(4) Uani 1 1 d . . . . .
C16 C 0.5207(3) 0.2681(2) 0.4031(2) 0.0584(5) Uani 1 1 d . . . . .
H16 H 0.469037 0.338005 0.384444 0.070 Uiso 1 1 calc R U . . .
C18 C 0.4619(3) 0.1252(2) 0.10806(19) 0.0529(5) Uani 1 1 d . . . . .
H18A H 0.577935 0.124669 0.140697 0.063 Uiso 1 1 calc R U . . .
H18B H 0.395191 0.036006 0.048167 0.063 Uiso 1 1 calc R U . . .
C20 C 0.7475(3) 0.4045(3) 0.1814(2) 0.0618(6) Uani 1 1 d . . . . .
H20 H 0.785814 0.328510 0.162160 0.074 Uiso 1 1 calc R U . . .
C21 C 0.2844(3) 0.2414(3) -0.00278(18) 0.0559(5) Uani 1 1 d . . . . .
H21A H 0.234268 0.166077 -0.074347 0.067 Uiso 1 1 calc R U . . .
H21B H 0.281835 0.333881 -0.023538 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5215(3) 0.5009(2) 0.1642(2) 0.0610(6) Uani 1 1 d . . . . .
H11 H 0.406731 0.492124 0.134949 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5825(3) 0.0516(3) 0.3494(2) 0.0618(6) Uani 1 1 d . . . . .
H3 H 0.569810 -0.026674 0.292794 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6241(3) 0.2786(3) 0.5171(2) 0.0731(7) Uani 1 1 d . . . . .
C7 C 0.7076(3) 0.1840(4) 0.5488(3) 0.0768(8) Uani 1 1 d . . . . .
H7 H 0.777581 0.195895 0.625770 0.092 Uiso 1 1 calc R U . . .
C15 C 0.6851(3) 0.0696(3) 0.4632(3) 0.0779(8) Uani 1 1 d . . . . .
H15 H 0.740848 0.002510 0.482676 0.093 Uiso 1 1 calc R U . . .
C2 C 0.8623(3) 0.5333(3) 0.2561(3) 0.0766(7) Uani 1 1 d . . . . .
H2 H 0.977044 0.542254 0.287492 0.092 Uiso 1 1 calc R U . . .
C17 C 0.6409(4) 0.6277(3) 0.2381(3) 0.0745(7) Uani 1 1 d . . . . .
C9 C 0.8122(4) 0.6490(3) 0.2856(3) 0.0792(8) Uani 1 1 d . . . . .
H9 H 0.890022 0.737098 0.335054 0.095 Uiso 1 1 calc R U . . .
C19 C -0.1861(4) 0.2973(4) -0.1008(3) 0.0823(8) Uani 1 1 d . . . . .
H19A H -0.183716 0.366129 -0.150250 0.123 Uiso 1 1 calc R U . . .
H19B H -0.226605 0.327115 -0.041517 0.123 Uiso 1 1 calc R U . . .
H19C H -0.261015 0.201736 -0.146696 0.123 Uiso 1 1 calc R U . . .
C5 C 0.0370(5) 0.2356(6) 0.3798(3) 0.1131(14) Uani 1 1 d . . . . .
H5A H -0.064186 0.150766 0.345763 0.170 Uiso 1 1 calc R U . . .
H5B H 0.005931 0.321078 0.393781 0.170 Uiso 1 1 calc R U . . .
H5C H 0.108349 0.223665 0.452346 0.170 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 C10 1.328(3) . ?
O1 C5 1.430(3) . ?
O4 C4 1.211(3) . ?
O5 C4 1.334(3) . ?
O5 C19 1.442(3) . ?
N1 C1 1.379(2) . ?
N1 C8 1.419(3) . ?
N1 C18 1.474(3) . ?
N2 C6 1.415(3) . ?
N2 C18 1.454(3) . ?
N2 C21 1.461(3) . ?
O3 C10 1.194(3) . ?
C1 C10 1.511(3) . ?
C1 C14 1.348(3) . ?
C4 C14 1.467(3) . ?
F2 C13 1.367(3) . ?
C6 C20 1.394(3) . ?
C6 C11 1.382(3) . ?
C8 C16 1.382(3) . ?
C8 C3 1.392(3) . ?
F12 C17 1.337(3) . ?
C14 C21 1.509(3) . ?
C16 H16 0.9300 . ?
C16 C13 1.390(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C2 1.372(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C17 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C15 1.372(4) . ?
C13 C7 1.348(4) . ?
C7 H7 0.9300 . ?
C7 C15 1.370(5) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C2 C9 1.371(4) . ?
C17 C9 1.372(4) . ?
C9 H9 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 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
C10 O1 C5 116.2(3) . . ?
C4 O5 C19 116.9(2) . . ?
C1 N1 C8 121.88(16) . . ?
C1 N1 C18 114.69(17) . . ?
C8 N1 C18 119.54(16) . . ?
C6 N2 C18 113.34(17) . . ?
C6 N2 C21 117.36(17) . . ?
C18 N2 C21 108.28(16) . . ?
N1 C1 C10 114.80(17) . . ?
C14 C1 N1 122.09(17) . . ?
C14 C1 C10 122.89(17) . . ?
O4 C4 O5 123.19(19) . . ?
O4 C4 C14 125.87(19) . . ?
O5 C4 C14 110.94(18) . . ?
C20 C6 N2 118.59(18) . . ?
C11 C6 N2 123.34(19) . . ?
C11 C6 C20 118.1(2) . . ?
C16 C8 N1 121.59(18) . . ?
C16 C8 C3 119.2(2) . . ?
C3 C8 N1 119.2(2) . . ?
O1 C10 C1 111.44(18) . . ?
O3 C10 O1 125.6(2) . . ?
O3 C10 C1 123.0(2) . . ?
C1 C14 C4 120.39(18) . . ?
C1 C14 C21 120.44(18) . . ?
C4 C14 C21 119.08(18) . . ?
C8 C16 H16 121.1 . . ?
C8 C16 C13 117.8(2) . . ?
C13 C16 H16 121.1 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N2 C18 N1 110.90(15) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
C6 C20 H20 119.5 . . ?
C2 C20 C6 120.9(2) . . ?
C2 C20 H20 119.5 . . ?
N2 C21 C14 112.25(17) . . ?
N2 C21 H21A 109.2 . . ?
N2 C21 H21B 109.2 . . ?
C14 C21 H21A 109.2 . . ?
C14 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C6 C11 H11 120.5 . . ?
C17 C11 C6 119.0(2) . . ?
C17 C11 H11 120.5 . . ?
C8 C3 H3 120.0 . . ?
C15 C3 C8 120.1(3) . . ?
C15 C3 H3 120.0 . . ?
F2 C13 C16 117.1(3) . . ?
C7 C13 F2 119.0(3) . . ?
C7 C13 C16 123.9(3) . . ?
C13 C7 H7 121.3 . . ?
C13 C7 C15 117.4(3) . . ?
C15 C7 H7 121.3 . . ?
C3 C15 H15 119.2 . . ?
C7 C15 C3 121.6(2) . . ?
C7 C15 H15 119.2 . . ?
C20 C2 H2 119.2 . . ?
C9 C2 C20 121.6(3) . . ?
C9 C2 H2 119.2 . . ?
F12 C17 C11 117.9(3) . . ?
F12 C17 C9 118.0(3) . . ?
C11 C17 C9 124.1(2) . . ?
C2 C9 C17 116.3(2) . . ?
C2 C9 H9 121.8 . . ?
C17 C9 H9 121.8 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O4 C4 C14 C1 -17.4(3) . . . . ?
O4 C4 C14 C21 159.2(2) . . . . ?
O5 C4 C14 C1 163.33(18) . . . . ?
O5 C4 C14 C21 -20.0(3) . . . . ?
N1 C1 C10 O1 119.93(19) . . . . ?
N1 C1 C10 O3 -57.8(3) . . . . ?
N1 C1 C14 C4 167.80(16) . . . . ?
N1 C1 C14 C21 -8.8(3) . . . . ?
N1 C8 C16 C13 178.1(2) . . . . ?
N1 C8 C3 C15 -179.10(19) . . . . ?
N2 C6 C20 C2 179.3(2) . . . . ?
N2 C6 C11 C17 -178.6(2) . . . . ?
C1 N1 C8 C16 -36.3(3) . . . . ?
C1 N1 C8 C3 144.3(2) . . . . ?
C1 N1 C18 N2 45.8(2) . . . . ?
C1 C14 C21 N2 -11.7(3) . . . . ?
C4 C14 C21 N2 171.66(17) . . . . ?
F2 C13 C7 C15 -177.7(3) . . . . ?
C6 N2 C18 N1 67.1(2) . . . . ?
C6 N2 C21 C14 -82.8(2) . . . . ?
C6 C20 C2 C9 -1.0(4) . . . . ?
C6 C11 C17 F12 178.6(3) . . . . ?
C6 C11 C17 C9 -0.4(4) . . . . ?
C8 N1 C1 C10 -35.9(2) . . . . ?
C8 N1 C1 C14 149.39(18) . . . . ?
C8 N1 C18 N2 -112.48(19) . . . . ?
C8 C16 C13 F2 179.0(2) . . . . ?
C8 C16 C13 C7 2.6(4) . . . . ?
C8 C3 C15 C7 -0.3(4) . . . . ?
C10 C1 C14 C4 -6.4(3) . . . . ?
C10 C1 C14 C21 176.99(18) . . . . ?
F12 C17 C9 C2 -179.6(3) . . . . ?
C14 C1 C10 O1 -65.4(2) . . . . ?
C14 C1 C10 O3 116.8(3) . . . . ?
C16 C8 C3 C15 1.5(3) . . . . ?
C16 C13 C7 C15 -1.4(4) . . . . ?
C18 N1 C1 C10 166.39(17) . . . . ?
C18 N1 C1 C14 -8.3(3) . . . . ?
C18 N1 C8 C16 120.3(2) . . . . ?
C18 N1 C8 C3 -59.0(3) . . . . ?
C18 N2 C6 C20 59.5(2) . . . . ?
C18 N2 C6 C11 -121.2(2) . . . . ?
C18 N2 C21 C14 47.0(2) . . . . ?
C20 C6 C11 C17 0.7(3) . . . . ?
C20 C2 C9 C17 1.2(4) . . . . ?
C21 N2 C6 C20 -173.01(18) . . . . ?
C21 N2 C6 C11 6.3(3) . . . . ?
C21 N2 C18 N1 -65.0(2) . . . . ?
C11 C6 C20 C2 -0.1(3) . . . . ?
C11 C17 C9 C2 -0.6(4) . . . . ?
C3 C8 C16 C13 -2.6(3) . . . . ?
C13 C7 C15 C3 0.2(4) . . . . ?
C19 O5 C4 O4 -4.5(3) . . . . ?
C19 O5 C4 C14 174.8(2) . . . . ?
C5 O1 C10 O3 -3.1(4) . . . . ?
C5 O1 C10 C1 179.3(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_230227hzs4f_0m
_database_code_depnum_ccdc_archive 'CCDC 2353759'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 F2 N2 O4'
_chemical_formula_sum            'C20 H18 F2 N2 O4'
_chemical_formula_weight         388.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5390(19)
_cell_length_b                   10.598(2)
_cell_length_c                   10.874(2)
_cell_angle_alpha                104.078(4)
_cell_angle_beta                 102.440(4)
_cell_angle_gamma                90.465(4)
_cell_volume                     930.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    862
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.784
_cell_measurement_theta_min      2.783
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0691 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.8264.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4691
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.428
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1557
_reflns_number_total             3247
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      0.930
_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)+(0.0458P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1256
_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:
 C10(H10A,H10B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C11(H11), C3(H3), C13(H13), C7(H7), C2(H2), C9(H9)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6612(3) 0.2497(2) 0.9567(2) 0.0489(6) Uani 1 1 d . . . . .
F1 F 0.2249(2) 0.5313(2) 0.5825(2) 0.0839(7) Uani 1 1 d . . . . .
O4 O 1.1484(3) 0.1349(2) 1.0108(2) 0.0571(7) Uani 1 1 d . . . . .
O2 O 0.9804(3) 0.2575(2) 1.1151(2) 0.0626(7) Uani 1 1 d . . . . .
O3 O 0.7226(3) 0.4654(2) 1.0302(2) 0.0627(7) Uani 1 1 d . . . . .
N1 N 0.8344(3) 0.4019(2) 0.7817(2) 0.0383(7) Uani 1 1 d . . . . .
F2 F 0.5949(3) -0.0455(2) 0.2686(2) 0.1057(9) Uani 1 1 d . . . . .
N2 N 1.0286(3) 0.2761(2) 0.6811(2) 0.0395(7) Uani 1 1 d . . . . .
C1 C 0.6769(4) 0.4329(3) 0.7263(3) 0.0362(8) Uani 1 1 d . . . . .
C4 C 0.8614(4) 0.3381(3) 0.8797(3) 0.0383(8) Uani 1 1 d . . . . .
C6 C 0.9907(4) 0.2655(3) 0.8989(3) 0.0394(8) Uani 1 1 d . . . . .
C8 C 0.7426(4) 0.3605(4) 0.9663(3) 0.0425(9) Uani 1 1 d . . . . .
C10 C 0.9675(4) 0.4045(3) 0.7162(3) 0.0427(9) Uani 1 1 d . . . . .
H10A H 0.930636 0.434963 0.638265 0.051 Uiso 1 1 calc R U . . .
H10B H 1.053578 0.465145 0.773315 0.051 Uiso 1 1 calc R U . . .
C12 C 0.9186(4) 0.1875(3) 0.5782(3) 0.0419(9) Uani 1 1 d . . . . .
C14 C 0.6551(4) 0.5544(3) 0.7004(3) 0.0439(9) Uani 1 1 d . . . . .
H14 H 0.742678 0.613591 0.716819 0.053 Uiso 1 1 calc R U . . .
C16 C 1.0329(4) 0.2229(3) 1.0194(4) 0.0473(9) Uani 1 1 d . . . . .
C18 C 0.5478(4) 0.3451(3) 0.7005(3) 0.0441(9) Uani 1 1 d . . . . .
H18 H 0.563604 0.262867 0.715337 0.053 Uiso 1 1 calc R U . . .
C20 C 1.0932(4) 0.2342(3) 0.7998(3) 0.0453(9) Uani 1 1 d . . . . .
H20A H 1.199819 0.276004 0.838904 0.054 Uiso 1 1 calc R U . . .
H20B H 1.103698 0.140820 0.776727 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3767(4) 0.4989(4) 0.6295(3) 0.0522(10) Uani 1 1 d . . . . .
C11 C 0.5018(4) 0.5866(3) 0.6500(3) 0.0525(10) Uani 1 1 d . . . . .
H11 H 0.485093 0.666894 0.630660 0.063 Uiso 1 1 calc R U . . .
C3 C 0.9038(4) 0.2033(3) 0.4531(4) 0.0543(10) Uani 1 1 d . . . . .
H3 H 0.967790 0.267494 0.439234 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3943(4) 0.3782(4) 0.6525(3) 0.0517(10) Uani 1 1 d . . . . .
H13 H 0.305830 0.319956 0.636339 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8255(4) 0.0887(3) 0.5948(4) 0.0568(10) Uani 1 1 d . . . . .
H7 H 0.834835 0.075187 0.677335 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7032(5) 0.0304(4) 0.3711(5) 0.0668(12) Uani 1 1 d . . . . .
C2 C 0.7182(5) 0.0096(4) 0.4900(5) 0.0687(12) Uani 1 1 d . . . . .
H2 H 0.656893 -0.057663 0.501754 0.082 Uiso 1 1 calc R U . . .
C17 C 1.2004(4) 0.0830(3) 1.1225(4) 0.0738(13) Uani 1 1 d . . . . .
H17A H 1.269125 0.013276 1.102269 0.111 Uiso 1 1 calc R U . . .
H17B H 1.108428 0.050454 1.145628 0.111 Uiso 1 1 calc R U . . .
H17C H 1.258395 0.150521 1.194192 0.111 Uiso 1 1 calc R U . . .
C9 C 0.7947(5) 0.1245(4) 0.3488(4) 0.0669(12) Uani 1 1 d . . . . .
H9 H 0.784411 0.135713 0.265246 0.080 Uiso 1 1 calc R U . . .
C19 C 0.5440(4) 0.2604(4) 1.0357(4) 0.0768(12) Uani 1 1 d . . . . .
H19A H 0.477992 0.180582 1.010921 0.115 Uiso 1 1 calc R U . . .
H19B H 0.477855 0.331037 1.023088 0.115 Uiso 1 1 calc R U . . .
H19C H 0.598039 0.276659 1.125619 0.115 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 1.330(4) . ?
O1 C19 1.441(4) . ?
F1 C5 1.367(3) . ?
O4 C16 1.365(4) . ?
O4 C17 1.440(3) . ?
O2 C16 1.198(4) . ?
O3 C8 1.195(4) . ?
N1 C1 1.426(3) . ?
N1 C4 1.376(4) . ?
N1 C10 1.469(4) . ?
F2 C15 1.361(4) . ?
N2 C10 1.453(4) . ?
N2 C12 1.428(4) . ?
N2 C20 1.464(3) . ?
C1 C14 1.388(4) . ?
C1 C18 1.373(4) . ?
C4 C6 1.359(4) . ?
C4 C8 1.509(4) . ?
C6 C16 1.462(4) . ?
C6 C20 1.508(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C3 1.390(4) . ?
C12 C7 1.378(4) . ?
C14 H14 0.9300 . ?
C14 C11 1.386(4) . ?
C18 H18 0.9300 . ?
C18 C13 1.384(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C5 C11 1.354(4) . ?
C5 C13 1.366(4) . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C3 C9 1.387(4) . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C7 C2 1.384(5) . ?
C15 C2 1.343(5) . ?
C15 C9 1.361(5) . ?
C2 H2 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C9 H9 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 O1 C19 115.3(3) . . ?
C16 O4 C17 115.9(3) . . ?
C1 N1 C10 121.4(3) . . ?
C4 N1 C1 121.6(3) . . ?
C4 N1 C10 115.2(2) . . ?
C10 N2 C20 109.1(3) . . ?
C12 N2 C10 112.7(2) . . ?
C12 N2 C20 117.8(3) . . ?
C14 C1 N1 119.1(3) . . ?
C18 C1 N1 120.7(3) . . ?
C18 C1 C14 120.2(3) . . ?
N1 C4 C8 115.2(3) . . ?
C6 C4 N1 121.4(3) . . ?
C6 C4 C8 123.4(3) . . ?
C4 C6 C16 119.0(3) . . ?
C4 C6 C20 120.4(3) . . ?
C16 C6 C20 120.5(3) . . ?
O1 C8 C4 110.8(3) . . ?
O3 C8 O1 125.7(3) . . ?
O3 C8 C4 123.4(3) . . ?
N1 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
N2 C10 N1 111.4(2) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C3 C12 N2 117.4(3) . . ?
C7 C12 N2 124.5(3) . . ?
C7 C12 C3 118.1(3) . . ?
C1 C14 H14 120.3 . . ?
C11 C14 C1 119.4(3) . . ?
C11 C14 H14 120.3 . . ?
O4 C16 C6 109.8(3) . . ?
O2 C16 O4 122.3(3) . . ?
O2 C16 C6 127.9(3) . . ?
C1 C18 H18 119.8 . . ?
C1 C18 C13 120.4(3) . . ?
C13 C18 H18 119.8 . . ?
N2 C20 C6 113.6(3) . . ?
N2 C20 H20A 108.9 . . ?
N2 C20 H20B 108.9 . . ?
C6 C20 H20A 108.9 . . ?
C6 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C11 C5 F1 118.9(3) . . ?
C11 C5 C13 123.3(3) . . ?
C13 C5 F1 117.8(4) . . ?
C14 C11 H11 120.6 . . ?
C5 C11 C14 118.7(3) . . ?
C5 C11 H11 120.6 . . ?
C12 C3 H3 119.6 . . ?
C9 C3 C12 120.9(4) . . ?
C9 C3 H3 119.6 . . ?
C18 C13 H13 121.0 . . ?
C5 C13 C18 118.0(3) . . ?
C5 C13 H13 121.0 . . ?
C12 C7 H7 119.6 . . ?
C12 C7 C2 120.8(4) . . ?
C2 C7 H7 119.6 . . ?
C2 C15 F2 119.5(4) . . ?
C2 C15 C9 122.1(4) . . ?
C9 C15 F2 118.4(4) . . ?
C7 C2 H2 120.2 . . ?
C15 C2 C7 119.5(4) . . ?
C15 C2 H2 120.2 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C9 H9 120.7 . . ?
C15 C9 C3 118.6(4) . . ?
C15 C9 H9 120.7 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
F1 C5 C11 C14 178.6(3) . . . . ?
F1 C5 C13 C18 -179.8(3) . . . . ?
N1 C1 C14 C11 -178.2(3) . . . . ?
N1 C1 C18 C13 176.9(3) . . . . ?
N1 C4 C6 C16 167.1(3) . . . . ?
N1 C4 C6 C20 -10.3(4) . . . . ?
N1 C4 C8 O1 116.7(3) . . . . ?
N1 C4 C8 O3 -60.7(4) . . . . ?
F2 C15 C2 C7 -178.4(3) . . . . ?
F2 C15 C9 C3 179.2(3) . . . . ?
N2 C12 C3 C9 -177.3(3) . . . . ?
N2 C12 C7 C2 178.0(3) . . . . ?
C1 N1 C4 C6 154.5(3) . . . . ?
C1 N1 C4 C8 -28.4(4) . . . . ?
C1 N1 C10 N2 -117.2(3) . . . . ?
C1 C14 C11 C5 1.2(5) . . . . ?
C1 C18 C13 C5 1.3(5) . . . . ?
C4 N1 C1 C14 137.7(3) . . . . ?
C4 N1 C1 C18 -41.3(4) . . . . ?
C4 N1 C10 N2 47.5(3) . . . . ?
C4 C6 C16 O4 170.3(3) . . . . ?
C4 C6 C16 O2 -10.8(5) . . . . ?
C4 C6 C20 N2 -6.4(4) . . . . ?
C6 C4 C8 O1 -66.2(4) . . . . ?
C6 C4 C8 O3 116.3(4) . . . . ?
C8 C4 C6 C16 -9.7(4) . . . . ?
C8 C4 C6 C20 172.8(3) . . . . ?
C10 N1 C1 C14 -58.5(4) . . . . ?
C10 N1 C1 C18 122.5(3) . . . . ?
C10 N1 C4 C6 -10.2(4) . . . . ?
C10 N1 C4 C8 166.9(2) . . . . ?
C10 N2 C12 C3 75.0(4) . . . . ?
C10 N2 C12 C7 -104.3(4) . . . . ?
C10 N2 C20 C6 41.6(3) . . . . ?
C12 N2 C10 N1 70.3(3) . . . . ?
C12 N2 C20 C6 -88.5(3) . . . . ?
C12 C3 C9 C15 -0.5(5) . . . . ?
C12 C7 C2 C15 -0.9(5) . . . . ?
C14 C1 C18 C13 -2.1(5) . . . . ?
C16 C6 C20 N2 176.1(3) . . . . ?
C18 C1 C14 C11 0.8(5) . . . . ?
C20 N2 C10 N1 -62.5(3) . . . . ?
C20 N2 C12 C3 -156.6(3) . . . . ?
C20 N2 C12 C7 24.1(4) . . . . ?
C20 C6 C16 O4 -12.2(4) . . . . ?
C20 C6 C16 O2 166.6(3) . . . . ?
C11 C5 C13 C18 0.8(5) . . . . ?
C3 C12 C7 C2 -1.3(5) . . . . ?
C13 C5 C11 C14 -2.0(5) . . . . ?
C7 C12 C3 C9 2.0(5) . . . . ?
C2 C15 C9 C3 -1.8(6) . . . . ?
C17 O4 C16 O2 1.8(4) . . . . ?
C17 O4 C16 C6 -179.2(3) . . . . ?
C9 C15 C2 C7 2.5(6) . . . . ?
C19 O1 C8 O3 -2.6(4) . . . . ?
C19 O1 C8 C4 -179.9(3) . . . . ?

_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_hzs-2
_database_code_depnum_ccdc_archive 'CCDC 2353620'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-08-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H28 N2 O6'
_chemical_formula_sum            'C24 H28 N2 O6'
_chemical_formula_weight         440.48
_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                   9.8663(3)
_cell_length_b                   11.2440(3)
_cell_length_c                   12.1222(4)
_cell_angle_alpha                64.929(3)
_cell_angle_beta                 89.007(2)
_cell_angle_gamma                67.849(3)
_cell_volume                     1111.81(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8017
_cell_measurement_temperature    150.01(11)
_cell_measurement_theta_max      71.1060
_cell_measurement_theta_min      4.0810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10620
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.566
_diffrn_reflns_theta_min         4.086
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  87.00   0.50    0.50    --   42.30 -38.00 -60.00  268
  2  ω    -12.00  86.00   0.50    0.50    --   42.30 -82.00  90.00  196
  3  ω     95.00 120.00   0.50    0.50    --   42.30  77.00-180.00   50
  4  ω     32.00  83.00   0.50    0.50    --   42.30 -82.00 150.00  102
  5  ω    -27.00  64.00   0.50    0.50    --   42.30 -82.00 -60.00  182
  6  ω      2.00  27.00   0.50    0.50    --   42.30 -82.00 150.00   50
  7  ω      4.00  30.00   0.50    0.50    --   42.30 -82.00-180.00   52
  8  ω     80.00 130.00   0.50    0.50    --   42.30  77.00-120.00  100
  9  ω     87.00 130.00   0.50    0.50    --   42.30  77.00  30.00   86
 10  ω     28.00 143.00   0.50    0.50    --  101.60 -82.00 -90.00  230
 11  ω     55.00 113.00   0.50    0.50    --  101.60 -82.00   0.00  116
 12  ω     13.00  47.00   0.50    0.50    --  101.60 -82.00   0.00   68
 13  ω     88.00 134.00   0.50    0.50    --  101.60 -64.00 -30.00   92
 14  ω     25.00 118.00   0.50    0.50    --  101.60 -82.00 120.00  186
 15  ω     12.00  84.00   0.50    0.50    --  101.60 -77.00 -60.00  144
 16  ω    145.00 170.00   0.50    0.50    --  101.60  12.00 -90.00   50
 17  ω     26.00  52.00   0.50    0.50    --  101.60 -82.00  60.00   52
 18  ω     12.00 140.00   0.50    0.50    --  101.60  12.00 -90.00  256
 19  ω     65.00 100.00   0.50    0.50    --  101.60 -82.00-120.00   70
 20  ω     77.00 102.00   0.50    0.50    --  101.60 -82.00  60.00   50
 21  ω     12.00  49.00   0.50    0.50    --  101.60 -82.00-120.00   74
 22  ω     32.00  58.00   0.50    0.50    --  101.60 -82.00-180.00   52
 23  ω     82.00 108.00   0.50    0.50    --  101.60 -82.00-180.00   52
 24  ω     79.00 104.00   0.50    0.50    --  101.60  50.00  30.00   50
 25  ω    165.00 191.00   0.50    0.50    --  101.60  50.00  30.00   52
 26  ω     82.00 107.00   0.50    0.50    --  101.60 -82.00 -60.00   50
 27  ω    123.00 190.00   0.50    0.50    --  101.60  64.00  90.00  134
 28  ω     87.00 120.00   0.50    0.50    --  101.60  82.00 -60.00   66
 29  ω     12.00 191.00   0.50    0.50    --  101.60  12.00 150.00  358
 30  ω     28.00 127.00   0.50    0.50    --  101.60 -64.00 120.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0870849000
_diffrn_orient_matrix_UB_12      -0.0135875000
_diffrn_orient_matrix_UB_13      -0.0951058000
_diffrn_orient_matrix_UB_21      0.1297762000
_diffrn_orient_matrix_UB_22      -0.0099188000
_diffrn_orient_matrix_UB_23      -0.0730763000
_diffrn_orient_matrix_UB_31      0.0695676000
_diffrn_orient_matrix_UB_32      -0.1648422000
_diffrn_orient_matrix_UB_33      0.0767114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3947
_reflns_number_total             4189
_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       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0113(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.043
_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)+(0.0469P)²+0.3026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0905
_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:
 C3(H3A,H3B), C4(H4A,H4B), C11(H11A,H11B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51058(10) 0.32170(9) 0.20783(8) 0.0324(2) Uani 1 1 d . . . . .
O2 O 0.35078(9) 0.42232(8) 0.30952(7) 0.02599(19) Uani 1 1 d . . . . .
O3 O 0.17270(10) 0.51190(9) 0.08249(9) 0.0365(2) Uani 1 1 d . . . . .
O4 O 0.04186(9) 0.74884(8) -0.03420(8) 0.02845(19) Uani 1 1 d . . . . .
O5 O 0.98935(9) 0.32622(9) 0.54074(7) 0.0293(2) Uani 1 1 d . . . . .
O6 O 0.30767(9) 0.97461(9) 0.42652(8) 0.0305(2) Uani 1 1 d . . . . .
N1 N 0.53608(10) 0.60259(10) 0.13534(8) 0.0233(2) Uani 1 1 d . . . . .
N2 N 0.38352(10) 0.85768(10) 0.01779(8) 0.0232(2) Uani 1 1 d . . . . .
C1 C 0.41209(12) 0.57646(11) 0.13217(10) 0.0214(2) Uani 1 1 d . . . . .
C2 C 0.28522(12) 0.67557(11) 0.05062(10) 0.0221(2) Uani 1 1 d . . . . .
C3 C 0.27029(12) 0.82785(12) -0.02941(10) 0.0236(2) Uani 1 1 d . . . . .
H3A H 0.280119 0.841380 -0.113198 0.028 Uiso 1 1 calc R U . . .
H3B H 0.172395 0.895378 -0.031599 0.028 Uiso 1 1 calc R U . . .
C4 C 0.52771(12) 0.74170(12) 0.03786(10) 0.0247(2) Uani 1 1 d . . . . .
H4A H 0.605303 0.763629 0.061716 0.030 Uiso 1 1 calc R U . . .
H4B H 0.544147 0.734420 -0.038587 0.030 Uiso 1 1 calc R U . . .
C5 C 0.64729(12) 0.52697(11) 0.24387(10) 0.0226(2) Uani 1 1 d . . . . .
C6 C 0.61455(12) 0.53584(12) 0.35241(10) 0.0250(2) Uani 1 1 d . . . . .
H6 H 0.517224 0.586922 0.357062 0.030 Uiso 1 1 calc R U . . .
C7 C 0.72557(12) 0.46921(12) 0.45466(10) 0.0248(2) Uani 1 1 d . . . . .
H7 H 0.702413 0.475198 0.527345 0.030 Uiso 1 1 calc R U . . .
C8 C 0.87123(12) 0.39368(11) 0.44745(10) 0.0233(2) Uani 1 1 d . . . . .
C9 C 0.90420(13) 0.38388(13) 0.33830(11) 0.0279(2) Uani 1 1 d . . . . .
H9 H 1.001383 0.332762 0.333372 0.034 Uiso 1 1 calc R U . . .
C10 C 0.79328(13) 0.44967(13) 0.23782(11) 0.0268(2) Uani 1 1 d . . . . .
H10 H 0.816040 0.442416 0.165536 0.032 Uiso 1 1 calc R U . . .
C11 C 0.96626(13) 0.34768(12) 0.64942(10) 0.0266(2) Uani 1 1 d . . . . .
H11A H 0.886509 0.321749 0.684447 0.032 Uiso 1 1 calc R U . . .
H11B H 0.939861 0.447776 0.629017 0.032 Uiso 1 1 calc R U . . .
C12 C 1.10965(15) 0.25310(14) 0.74046(12) 0.0369(3) Uani 1 1 d . . . . .
H12A H 1.187714 0.279499 0.704618 0.055 Uiso 1 1 calc R U . . .
H12B H 1.134171 0.154369 0.760361 0.055 Uiso 1 1 calc R U . . .
H12C H 1.098323 0.265231 0.814331 0.055 Uiso 1 1 calc R U . . .
C13 C 0.35741(12) 0.88608(11) 0.12253(10) 0.0220(2) Uani 1 1 d . . . . .
C14 C 0.23873(12) 0.87738(12) 0.18386(10) 0.0249(2) Uani 1 1 d . . . . .
H14 H 0.171316 0.852113 0.156339 0.030 Uiso 1 1 calc R U . . .
C15 C 0.21834(13) 0.90563(12) 0.28568(11) 0.0270(2) Uani 1 1 d . . . . .
H15 H 0.138118 0.898968 0.325404 0.032 Uiso 1 1 calc R U . . .
C16 C 0.31779(13) 0.94373(12) 0.32788(10) 0.0252(2) Uani 1 1 d . . . . .
C17 C 0.43589(13) 0.95546(12) 0.26573(10) 0.0263(2) Uani 1 1 d . . . . .
H17 H 0.502225 0.982361 0.292495 0.032 Uiso 1 1 calc R U . . .
C18 C 0.45513(12) 0.92751(12) 0.16495(10) 0.0248(2) Uani 1 1 d . . . . .
H18 H 0.534258 0.936245 0.124348 0.030 Uiso 1 1 calc R U . . .
C19 C 0.20217(15) 0.94406(17) 0.50184(13) 0.0406(3) Uani 1 1 d . . . . .
H19A H 0.222125 0.842899 0.534805 0.049 Uiso 1 1 calc R U . . .
H19B H 0.103009 1.000063 0.453355 0.049 Uiso 1 1 calc R U . . .
C20 C 0.21258(15) 0.98130(15) 0.60546(12) 0.0366(3) Uani 1 1 d . . . . .
H20A H 0.189057 1.082247 0.572223 0.055 Uiso 1 1 calc R U . . .
H20B H 0.311632 0.927194 0.651768 0.055 Uiso 1 1 calc R U . . .
H20C H 0.143711 0.958305 0.658752 0.055 Uiso 1 1 calc R U . . .
C21 C 0.43028(12) 0.42537(11) 0.21907(10) 0.0225(2) Uani 1 1 d . . . . .
C22 C 0.34893(15) 0.28333(13) 0.38697(12) 0.0356(3) Uani 1 1 d . . . . .
H22A H 0.312562 0.251411 0.336563 0.053 Uiso 1 1 calc R U . . .
H22B H 0.285233 0.291468 0.446536 0.053 Uiso 1 1 calc R U . . .
H22C H 0.447777 0.215079 0.429104 0.053 Uiso 1 1 calc R U . . .
C23 C 0.16560(12) 0.63347(12) 0.03763(10) 0.0235(2) Uani 1 1 d . . . . .
C24 C -0.08229(13) 0.71833(13) -0.05550(12) 0.0322(3) Uani 1 1 d . . . . .
H24A H -0.060442 0.670936 -0.107528 0.048 Uiso 1 1 calc R U . . .
H24B H -0.169299 0.806689 -0.095182 0.048 Uiso 1 1 calc R U . . .
H24C H -0.099602 0.657085 0.022043 0.048 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 C21 1.1998(13) . ?
O2 C21 1.3332(13) . ?
O2 C22 1.4496(13) . ?
O3 C23 1.2117(14) . ?
O4 C23 1.3479(14) . ?
O4 C24 1.4449(13) . ?
O5 C8 1.3655(13) . ?
O5 C11 1.4365(13) . ?
O6 C16 1.3718(13) . ?
O6 C19 1.4163(15) . ?
N1 C1 1.3662(14) . ?
N1 C4 1.4796(14) . ?
N1 C5 1.4339(14) . ?
N2 C3 1.4681(13) . ?
N2 C4 1.4587(14) . ?
N2 C13 1.4320(14) . ?
C1 C2 1.3577(15) . ?
C1 C21 1.5125(15) . ?
C2 C3 1.5171(14) . ?
C2 C23 1.4604(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.3847(15) . ?
C5 C10 1.3935(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.3923(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3901(16) . ?
C8 C9 1.3965(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.3785(16) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5084(17) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.3885(15) . ?
C13 C18 1.4036(15) . ?
C14 H14 0.9300 . ?
C14 C15 1.3929(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3885(16) . ?
C16 C17 1.3943(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.3783(16) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.4987(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C21 O2 C22 114.68(9) . . ?
C23 O4 C24 115.64(9) . . ?
C8 O5 C11 118.20(8) . . ?
C16 O6 C19 117.27(9) . . ?
C1 N1 C4 115.77(9) . . ?
C1 N1 C5 122.44(9) . . ?
C5 N1 C4 118.99(9) . . ?
C4 N2 C3 107.92(8) . . ?
C13 N2 C3 116.18(8) . . ?
C13 N2 C4 112.95(8) . . ?
N1 C1 C21 115.11(9) . . ?
C2 C1 N1 122.37(10) . . ?
C2 C1 C21 122.35(9) . . ?
C1 C2 C3 120.00(9) . . ?
C1 C2 C23 119.64(10) . . ?
C23 C2 C3 120.33(9) . . ?
N2 C3 C2 111.44(9) . . ?
N2 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
N2 C4 N1 111.20(8) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 N1 121.44(10) . . ?
C6 C5 C10 119.25(10) . . ?
C10 C5 N1 119.21(9) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.81(10) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.61(10) . . ?
C8 C7 H7 120.2 . . ?
O5 C8 C7 124.81(10) . . ?
O5 C8 C9 115.57(9) . . ?
C7 C8 C9 119.62(10) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.28(10) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.43(10) . . ?
C9 C10 H10 119.8 . . ?
O5 C11 H11A 110.3 . . ?
O5 C11 H11B 110.3 . . ?
O5 C11 C12 107.24(9) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 123.65(10) . . ?
C14 C13 C18 117.70(10) . . ?
C18 C13 N2 118.64(9) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.50(10) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.01(10) . . ?
C16 C15 H15 120.0 . . ?
O6 C16 C15 124.78(10) . . ?
O6 C16 C17 116.13(10) . . ?
C15 C16 C17 119.07(10) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.54(10) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.16(10) . . ?
C17 C18 H18 119.4 . . ?
O6 C19 H19A 110.0 . . ?
O6 C19 H19B 110.0 . . ?
O6 C19 C20 108.59(11) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 O2 125.07(10) . . ?
O1 C21 C1 122.85(10) . . ?
O2 C21 C1 112.06(9) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 O4 122.52(10) . . ?
O3 C23 C2 126.21(10) . . ?
O4 C23 C2 111.26(9) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O5 C8 C9 C10 -179.21(10) . . . . ?
O6 C16 C17 C18 -179.62(10) . . . . ?
N1 C1 C2 C3 -8.26(15) . . . . ?
N1 C1 C2 C23 169.73(9) . . . . ?
N1 C1 C21 O1 -65.84(14) . . . . ?
N1 C1 C21 O2 112.35(10) . . . . ?
N1 C5 C6 C7 -175.93(10) . . . . ?
N1 C5 C10 C9 175.69(10) . . . . ?
N2 C13 C14 C15 179.79(10) . . . . ?
N2 C13 C18 C17 -179.65(10) . . . . ?
C1 N1 C4 N2 41.62(12) . . . . ?
C1 N1 C5 C6 -61.92(14) . . . . ?
C1 N1 C5 C10 121.86(11) . . . . ?
C1 C2 C3 N2 -15.90(14) . . . . ?
C1 C2 C23 O3 -9.39(17) . . . . ?
C1 C2 C23 O4 171.61(9) . . . . ?
C2 C1 C21 O1 109.55(13) . . . . ?
C2 C1 C21 O2 -72.26(13) . . . . ?
C3 N2 C4 N1 -64.36(11) . . . . ?
C3 N2 C13 C14 4.31(14) . . . . ?
C3 N2 C13 C18 -174.55(9) . . . . ?
C3 C2 C23 O3 168.58(11) . . . . ?
C3 C2 C23 O4 -10.42(14) . . . . ?
C4 N1 C1 C2 -4.59(14) . . . . ?
C4 N1 C1 C21 170.80(8) . . . . ?
C4 N1 C5 C6 98.31(12) . . . . ?
C4 N1 C5 C10 -77.92(13) . . . . ?
C4 N2 C3 C2 50.43(11) . . . . ?
C4 N2 C13 C14 -121.19(11) . . . . ?
C4 N2 C13 C18 59.95(12) . . . . ?
C5 N1 C1 C2 156.23(10) . . . . ?
C5 N1 C1 C21 -28.39(14) . . . . ?
C5 N1 C4 N2 -119.90(10) . . . . ?
C5 C6 C7 C8 0.44(16) . . . . ?
C6 C5 C10 C9 -0.62(17) . . . . ?
C6 C7 C8 O5 178.87(10) . . . . ?
C6 C7 C8 C9 -0.86(16) . . . . ?
C7 C8 C9 C10 0.54(17) . . . . ?
C8 O5 C11 C12 175.68(9) . . . . ?
C8 C9 C10 C5 0.20(18) . . . . ?
C10 C5 C6 C7 0.29(16) . . . . ?
C11 O5 C8 C7 -7.59(15) . . . . ?
C11 O5 C8 C9 172.15(9) . . . . ?
C13 N2 C3 C2 -77.57(11) . . . . ?
C13 N2 C4 N1 65.48(11) . . . . ?
C13 C14 C15 C16 0.11(17) . . . . ?
C14 C13 C18 C17 1.42(16) . . . . ?
C14 C15 C16 O6 179.57(10) . . . . ?
C14 C15 C16 C17 1.07(17) . . . . ?
C15 C16 C17 C18 -0.99(17) . . . . ?
C16 O6 C19 C20 178.28(10) . . . . ?
C16 C17 C18 C13 -0.27(17) . . . . ?
C18 C13 C14 C15 -1.34(16) . . . . ?
C19 O6 C16 C15 10.21(17) . . . . ?
C19 O6 C16 C17 -171.25(11) . . . . ?
C21 C1 C2 C3 176.69(9) . . . . ?
C21 C1 C2 C23 -5.33(15) . . . . ?
C22 O2 C21 O1 -9.10(16) . . . . ?
C22 O2 C21 C1 172.76(9) . . . . ?
C23 C2 C3 N2 166.13(9) . . . . ?
C24 O4 C23 O3 -0.55(16) . . . . ?
C24 O4 C23 C2 178.49(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.689
####################################################################### 
# 
# 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_mo_240423hsz5_0m
_database_code_depnum_ccdc_archive 'CCDC 2353771'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_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         'C24 H22 F6 N2 O4'
_chemical_formula_sum            'C24 H22 F6 N2 O4'
_chemical_formula_weight         516.43
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.7459(6)
_cell_length_b                   8.0948(5)
_cell_length_c                   14.1993(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.606(2)
_cell_angle_gamma                90
_cell_volume                     1209.89(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3778
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      21.789
_cell_measurement_theta_min      2.179
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1294 before and 0.0703 after correction.
The Ratio of minimum to maximum transmission is 0.9166.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12174
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         2.179
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                3194
_reflns_number_total             5745
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5745
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0753
_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)+(0.1338P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2127
_refine_ls_wR_factor_ref         0.2510
_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:
 C10(H10A,H10B), C13(H13A,H13B), C19(H19A,H19B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C20(H20), C7(H7), C1(H1), C5(H5), C17(H17), C9(H9)
2.c Fitted hexagon refined as free rotating group:
 C2(C4,C12,C20,C22,C7), C1(C3,C5,C17,C24,C9)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9164(3) 0.2731(6) 0.5336(3) 0.0664(10) Uani 1 1 d . . . . .
O4 O 0.6017(4) 0.1222(6) 0.3929(3) 0.0772(12) Uani 1 1 d . . . . .
O2 O 0.7528(4) 0.4094(6) 0.4458(3) 0.0771(12) Uani 1 1 d . . . . .
N1 N 0.7827(4) 0.2306(5) 0.6758(3) 0.0553(10) Uani 1 1 d . . . . .
O3 O 0.4267(4) 0.2500(7) 0.4190(3) 0.0837(14) Uani 1 1 d . . . . .
N2 N 0.5809(4) 0.1892(7) 0.7173(3) 0.0632(12) Uani 1 1 d . . . . .
C6 C 0.7192(5) 0.2484(7) 0.5788(3) 0.0546(12) Uani 1 1 d . . . . .
C8 C 0.7957(5) 0.3193(7) 0.5111(4) 0.0554(12) Uani 1 1 d . . . . .
F1 F 0.9663(7) 0.8995(8) 0.8884(6) 0.158(3) Uani 1 1 d . . . . .
C10 C 0.5124(5) 0.1653(7) 0.6196(4) 0.0586(13) Uani 1 1 d . . . . .
H10A H 0.438822 0.237292 0.606958 0.070 Uiso 1 1 calc R U . . .
H10B H 0.482908 0.051949 0.611182 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5970(5) 0.2027(7) 0.5499(4) 0.0566(12) Uani 1 1 d . . . . .
C16 C 0.5327(5) 0.1965(7) 0.4476(4) 0.0581(12) Uani 1 1 d . . . . .
C18 C 0.3082(7) 0.2199(11) 1.0194(5) 0.086(2) Uani 1 1 d . . . . .
F4 F 0.3614(8) 0.1678(19) 1.0974(4) 0.255(7) Uani 1 1 d . . . . .
F6 F 0.1962(7) 0.1578(13) 0.9997(5) 0.179(4) Uani 1 1 d . . . . .
C13 C 0.7115(5) 0.1288(8) 0.7293(4) 0.0633(13) Uani 1 1 d . . . . .
H13A H 0.751672 0.130557 0.796884 0.076 Uiso 1 1 calc R U . . .
H13B H 0.711000 0.015562 0.706833 0.076 Uiso 1 1 calc R U . . .
C15 C 1.0382(8) 0.7865(12) 0.8666(7) 0.097(2) Uani 1 1 d . . . . .
C2 C 0.9435(4) 0.3464(4) 0.8028(3) 0.0714(16) Uani 1 1 d G . . . .
H2 H 0.966851 0.239954 0.823937 0.086 Uiso 1 1 calc R U . . .
C4 C 0.8452(3) 0.3700(4) 0.7238(2) 0.0508(11) Uani 1 1 d G . . . .
C12 C 0.8103(3) 0.5290(4) 0.6922(2) 0.0588(13) Uani 1 1 d G . . . .
H12 H 0.744606 0.544864 0.639341 0.071 Uiso 1 1 calc R U . . .
C20 C 0.8737(4) 0.6644(3) 0.7395(3) 0.0689(15) Uani 1 1 d G . . . .
H20 H 0.850339 0.770851 0.718322 0.083 Uiso 1 1 calc R U . . .
C22 C 0.9719(4) 0.6408(4) 0.8185(3) 0.0680(14) Uani 1 1 d G . . . .
C7 C 1.0068(3) 0.4818(5) 0.8501(2) 0.0764(18) Uani 1 1 d G . . . .
H7 H 1.072585 0.465945 0.902919 0.092 Uiso 1 1 calc R U . . .
C1 C 0.5094(4) 0.2502(5) 0.9578(2) 0.0758(17) Uani 1 1 d G . . . .
H1 H 0.549930 0.287118 1.018250 0.091 Uiso 1 1 calc R U . . .
C3 C 0.3822(3) 0.2044(6) 0.9418(2) 0.0703(15) Uani 1 1 d G . . . .
C5 C 0.3215(3) 0.1491(6) 0.8515(3) 0.0763(17) Uani 1 1 d G . . . .
H5 H 0.236410 0.118511 0.840787 0.092 Uiso 1 1 calc R U . . .
C17 C 0.3881(3) 0.1397(6) 0.7773(2) 0.0711(15) Uani 1 1 d G . . . .
H17 H 0.347474 0.102723 0.716857 0.085 Uiso 1 1 calc R U . . .
C24 C 0.5152(3) 0.1855(6) 0.7933(2) 0.0592(13) Uani 1 1 d G . . . .
C9 C 0.5759(3) 0.2407(5) 0.8836(2) 0.0732(16) Uani 1 1 d G . . . .
H9 H 0.660996 0.271330 0.894318 0.088 Uiso 1 1 calc R U . . .
C19 C 0.5540(8) 0.1277(11) 0.2903(4) 0.0845(19) Uani 1 1 d . . . . .
H19A H 0.515645 0.234408 0.271861 0.101 Uiso 1 1 calc R U . . .
H19B H 0.490021 0.042922 0.271426 0.101 Uiso 1 1 calc R U . . .
F3 F 1.0983(11) 0.8658(13) 0.8135(9) 0.249(7) Uani 1 1 d . . . . .
F2 F 0.2778(9) 0.3733(11) 1.0332(6) 0.177(3) Uani 1 1 d . . . . .
C21 C 1.0013(7) 0.3407(12) 0.4746(6) 0.094(2) Uani 1 1 d . . . . .
H21A H 0.994210 0.276563 0.416024 0.112 Uiso 1 1 calc R U . . .
H21B H 0.977815 0.453925 0.457050 0.112 Uiso 1 1 calc R U . . .
C11 C 0.6629(9) 0.0995(16) 0.2424(5) 0.111(3) Uani 1 1 d . . . . .
H11A H 0.637401 0.122543 0.174952 0.166 Uiso 1 1 calc R U . . .
H11B H 0.690003 -0.013504 0.251176 0.166 Uiso 1 1 calc R U . . .
H11C H 0.731824 0.171057 0.270104 0.166 Uiso 1 1 calc R U . . .
F5 F 1.1163(13) 0.7580(10) 0.9406(10) 0.308(9) Uani 1 1 d . . . . .
C23 C 1.1315(7) 0.3347(12) 0.5293(7) 0.106(3) Uani 1 1 d . . . . .
H23A H 1.188090 0.376810 0.490640 0.159 Uiso 1 1 calc R U . . .
H23B H 1.153815 0.222461 0.547074 0.159 Uiso 1 1 calc R U . . .
H23C H 1.138418 0.400781 0.586260 0.159 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 1.326(6) . ?
O1 C21 1.464(8) . ?
O4 C16 1.321(7) . ?
O4 C19 1.444(7) . ?
O2 C8 1.197(7) . ?
N1 C6 1.416(6) . ?
N1 C13 1.441(7) . ?
N1 C4 1.416(5) . ?
O3 C16 1.210(7) . ?
N2 C10 1.447(7) . ?
N2 C13 1.463(7) . ?
N2 C24 1.404(5) . ?
C6 C8 1.499(8) . ?
C6 C14 1.346(7) . ?
F1 C15 1.275(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C14 1.503(8) . ?
C14 C16 1.479(7) . ?
C18 F4 1.215(9) . ?
C18 F6 1.282(10) . ?
C18 C3 1.488(8) . ?
C18 F2 1.309(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C22 1.473(9) . ?
C15 F3 1.262(12) . ?
C15 F5 1.228(11) . ?
C2 H2 0.9300 . ?
C2 C4 1.3900 . ?
C2 C7 1.3900 . ?
C4 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C22 1.3900 . ?
C22 C7 1.3900 . ?
C7 H7 0.9300 . ?
C1 H1 0.9300 . ?
C1 C3 1.3900 . ?
C1 C9 1.3900 . ?
C3 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C24 1.3900 . ?
C24 C9 1.3900 . ?
C9 H9 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C11 1.485(11) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C23 1.459(11) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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 O1 C21 116.6(5) . . ?
C16 O4 C19 116.9(5) . . ?
C6 N1 C13 111.6(4) . . ?
C6 N1 C4 118.5(4) . . ?
C4 N1 C13 116.9(4) . . ?
C10 N2 C13 111.0(5) . . ?
C24 N2 C10 119.8(4) . . ?
C24 N2 C13 121.5(4) . . ?
N1 C6 C8 116.3(4) . . ?
C14 C6 N1 121.2(5) . . ?
C14 C6 C8 122.5(5) . . ?
O1 C8 C6 111.9(5) . . ?
O2 C8 O1 124.4(5) . . ?
O2 C8 C6 123.7(5) . . ?
N2 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
N2 C10 C14 110.2(4) . . ?
H10A C10 H10B 108.1 . . ?
C14 C10 H10A 109.6 . . ?
C14 C10 H10B 109.6 . . ?
C6 C14 C10 122.5(5) . . ?
C6 C14 C16 122.9(5) . . ?
C16 C14 C10 114.5(4) . . ?
O4 C16 C14 112.7(4) . . ?
O3 C16 O4 124.5(5) . . ?
O3 C16 C14 122.7(5) . . ?
F4 C18 F6 108.1(10) . . ?
F4 C18 C3 115.0(7) . . ?
F4 C18 F2 106.2(10) . . ?
F6 C18 C3 115.1(6) . . ?
F6 C18 F2 98.8(8) . . ?
F2 C18 C3 112.2(7) . . ?
N1 C13 N2 110.2(5) . . ?
N1 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
N2 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
F1 C15 C22 115.3(7) . . ?
F3 C15 F1 100.9(10) . . ?
F3 C15 C22 112.8(7) . . ?
F5 C15 F1 105.7(10) . . ?
F5 C15 C22 115.5(9) . . ?
F5 C15 F3 105.3(11) . . ?
C4 C2 H2 120.0 . . ?
C4 C2 C7 120.0 . . ?
C7 C2 H2 120.0 . . ?
C2 C4 N1 119.3(3) . . ?
C2 C4 C12 120.0 . . ?
C12 C4 N1 120.7(3) . . ?
C4 C12 H12 120.0 . . ?
C4 C12 C20 120.0 . . ?
C20 C12 H12 120.0 . . ?
C12 C20 H20 120.0 . . ?
C22 C20 C12 120.0 . . ?
C22 C20 H20 120.0 . . ?
C20 C22 C15 118.8(5) . . ?
C20 C22 C7 120.0 . . ?
C7 C22 C15 121.2(5) . . ?
C2 C7 H7 120.0 . . ?
C22 C7 C2 120.0 . . ?
C22 C7 H7 120.0 . . ?
C3 C1 H1 120.0 . . ?
C3 C1 C9 120.0 . . ?
C9 C1 H1 120.0 . . ?
C1 C3 C18 120.7(4) . . ?
C5 C3 C18 119.3(4) . . ?
C5 C3 C1 120.0 . . ?
C3 C5 H5 120.0 . . ?
C3 C5 C17 120.0 . . ?
C17 C5 H5 120.0 . . ?
C5 C17 H17 120.0 . . ?
C24 C17 C5 120.0 . . ?
C24 C17 H17 120.0 . . ?
C17 C24 N2 120.7(3) . . ?
C17 C24 C9 120.0 . . ?
C9 C24 N2 119.2(3) . . ?
C1 C9 H9 120.0 . . ?
C24 C9 C1 120.0 . . ?
C24 C9 H9 120.0 . . ?
O4 C19 H19A 110.2 . . ?
O4 C19 H19B 110.2 . . ?
O4 C19 C11 107.7(6) . . ?
H19A C19 H19B 108.5 . . ?
C11 C19 H19A 110.2 . . ?
C11 C19 H19B 110.2 . . ?
O1 C21 H21A 109.9 . . ?
O1 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C23 C21 O1 108.9(6) . . ?
C23 C21 H21A 109.9 . . ?
C23 C21 H21B 109.9 . . ?
C19 C11 H11A 109.5 . . ?
C19 C11 H11B 109.5 . . ?
C19 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C6 C8 O1 34.5(6) . . . . ?
N1 C6 C8 O2 -144.2(6) . . . . ?
N1 C6 C14 C10 13.5(8) . . . . ?
N1 C6 C14 C16 -171.0(5) . . . . ?
N1 C4 C12 C20 -179.3(4) . . . . ?
N2 C10 C14 C6 1.2(7) . . . . ?
N2 C10 C14 C16 -174.8(5) . . . . ?
N2 C24 C9 C1 175.0(4) . . . . ?
C6 N1 C13 N2 -51.9(6) . . . . ?
C6 N1 C4 C2 -156.8(3) . . . . ?
C6 N1 C4 C12 22.5(5) . . . . ?
C6 C14 C16 O4 46.5(7) . . . . ?
C6 C14 C16 O3 -135.6(6) . . . . ?
C8 O1 C21 C23 157.3(7) . . . . ?
C8 C6 C14 C10 -167.0(5) . . . . ?
C8 C6 C14 C16 8.6(8) . . . . ?
F1 C15 C22 C20 50.2(10) . . . . ?
F1 C15 C22 C7 -130.4(8) . . . . ?
C10 N2 C13 N1 67.8(6) . . . . ?
C10 N2 C24 C17 7.7(6) . . . . ?
C10 N2 C24 C9 -167.2(4) . . . . ?
C10 C14 C16 O4 -137.6(5) . . . . ?
C10 C14 C16 O3 40.2(8) . . . . ?
C14 C6 C8 O1 -145.1(5) . . . . ?
C14 C6 C8 O2 36.2(9) . . . . ?
C16 O4 C19 C11 158.1(7) . . . . ?
C18 C3 C5 C17 177.7(5) . . . . ?
F4 C18 C3 C1 -46.2(12) . . . . ?
F4 C18 C3 C5 136.1(10) . . . . ?
F6 C18 C3 C1 -172.9(7) . . . . ?
F6 C18 C3 C5 9.5(10) . . . . ?
C13 N1 C6 C8 -166.9(5) . . . . ?
C13 N1 C6 C14 12.7(7) . . . . ?
C13 N1 C4 C2 65.1(5) . . . . ?
C13 N1 C4 C12 -115.6(4) . . . . ?
C13 N2 C10 C14 -39.9(6) . . . . ?
C13 N2 C24 C17 -138.8(4) . . . . ?
C13 N2 C24 C9 46.3(6) . . . . ?
C15 C22 C7 C2 -179.4(5) . . . . ?
C2 C4 C12 C20 0.0 . . . . ?
C4 N1 C6 C8 52.8(6) . . . . ?
C4 N1 C6 C14 -127.6(5) . . . . ?
C4 N1 C13 N2 88.9(5) . . . . ?
C4 C2 C7 C22 0.0 . . . . ?
C4 C12 C20 C22 0.0 . . . . ?
C12 C20 C22 C15 179.4(5) . . . . ?
C12 C20 C22 C7 0.0 . . . . ?
C20 C22 C7 C2 0.0 . . . . ?
C7 C2 C4 N1 179.3(4) . . . . ?
C7 C2 C4 C12 0.0 . . . . ?
C1 C3 C5 C17 0.0 . . . . ?
C3 C1 C9 C24 0.0 . . . . ?
C3 C5 C17 C24 0.0 . . . . ?
C5 C17 C24 N2 -174.9(4) . . . . ?
C5 C17 C24 C9 0.0 . . . . ?
C17 C24 C9 C1 0.0 . . . . ?
C24 N2 C10 C14 170.4(5) . . . . ?
C24 N2 C13 N1 -143.1(5) . . . . ?
C9 C1 C3 C18 -177.6(5) . . . . ?
C9 C1 C3 C5 0.0 . . . . ?
C19 O4 C16 O3 9.5(9) . . . . ?
C19 O4 C16 C14 -172.7(6) . . . . ?
F3 C15 C22 C20 -65.0(11) . . . . ?
F3 C15 C22 C7 114.4(10) . . . . ?
F2 C18 C3 C1 75.2(8) . . . . ?
F2 C18 C3 C5 -102.4(8) . . . . ?
C21 O1 C8 O2 1.1(9) . . . . ?
C21 O1 C8 C6 -177.6(5) . . . . ?
F5 C15 C22 C20 173.9(11) . . . . ?
F5 C15 C22 C7 -6.7(13) . . . . ?

_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_mo_240423hsz1_0m
_database_code_depnum_ccdc_archive 'CCDC 2353768'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_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         'C20 H18 F2 N2 O4'
_chemical_formula_sum            'C20 H18 F2 N2 O4'
_chemical_formula_weight         388.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5188(4)
_cell_length_b                   9.7000(4)
_cell_length_c                   11.0300(4)
_cell_angle_alpha                80.686(2)
_cell_angle_beta                 85.148(2)
_cell_angle_gamma                68.439(2)
_cell_volume                     934.33(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7945
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      28.089
_cell_measurement_theta_min      2.280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1115 before and 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.8863.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32399
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3442
_reflns_number_total             4636
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.045
_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)+(0.0636P)²+0.1703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1340
_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:
 C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C9(H9), C11(H11), C13(H13), C15(H15), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.35201(11) 1.08471(11) 0.81441(9) 0.0628(3) Uani 1 1 d . . . . .
F2 F -0.11806(13) 0.99986(15) 0.82668(12) 0.0846(4) Uani 1 1 d . . . . .
O1 O 0.23484(12) 0.52971(11) 0.60594(10) 0.0512(3) Uani 1 1 d . . . . .
O2 O 0.20161(14) 0.67685(13) 0.35364(10) 0.0581(3) Uani 1 1 d . . . . .
O3 O -0.01120(13) 0.67379(14) 0.60678(13) 0.0659(3) Uani 1 1 d . . . . .
O4 O 0.39083(12) 0.76363(13) 0.30827(10) 0.0551(3) Uani 1 1 d . . . . .
N1 N 0.30241(13) 0.99652(13) 0.60273(10) 0.0414(3) Uani 1 1 d . . . . .
N2 N 0.12465(13) 0.87595(13) 0.67908(10) 0.0401(3) Uani 1 1 d . . . . .
C1 C 0.17048(15) 0.79065(14) 0.58448(12) 0.0378(3) Uani 1 1 d . . . . .
C2 C 0.4260(2) 0.6933(2) 0.19923(18) 0.0726(5) Uani 1 1 d . . . . .
H2A H 0.344686 0.741190 0.143145 0.109 Uiso 1 1 calc R U . . .
H2B H 0.439673 0.589343 0.220350 0.109 Uiso 1 1 calc R U . . .
H2C H 0.517308 0.702409 0.161148 0.109 Uiso 1 1 calc R U . . .
C3 C 0.5752(2) 0.8773(2) 0.85403(16) 0.0601(4) Uani 1 1 d . . . . .
H3 H 0.587889 0.914400 0.923332 0.072 Uiso 1 1 calc R U . . .
C4 C 0.42570(15) 0.90425(15) 0.67782(12) 0.0398(3) Uani 1 1 d . . . . .
C5 C -0.01106(19) 0.8730(2) 0.87452(15) 0.0549(4) Uani 1 1 d . . . . .
C6 C 0.11234(16) 0.80795(16) 0.80146(12) 0.0428(3) Uani 1 1 d . . . . .
C7 C 0.6805(2) 0.7458(2) 0.82223(19) 0.0652(5) Uani 1 1 d . . . . .
H7 H 0.765707 0.694055 0.869111 0.078 Uiso 1 1 calc R U . . .
C8 C 0.11952(16) 0.65893(16) 0.59895(13) 0.0427(3) Uani 1 1 d . . . . .
C9 C 0.0833(3) 0.6806(3) 1.04151(18) 0.0875(7) Uani 1 1 d . . . . .
H9 H 0.073612 0.637275 1.121854 0.105 Uiso 1 1 calc R U . . .
C10 C 0.27343(17) 0.74784(16) 0.37804(13) 0.0436(3) Uani 1 1 d . . . . .
C11 C 0.2233(2) 0.6766(2) 0.85206(16) 0.0620(4) Uani 1 1 d . . . . .
H11 H 0.308705 0.630743 0.805111 0.074 Uiso 1 1 calc R U . . .
C12 C 0.24628(15) 0.82934(15) 0.48375(12) 0.0405(3) Uani 1 1 d . . . . .
C13 C 0.65822(19) 0.69221(19) 0.72084(19) 0.0603(4) Uani 1 1 d . . . . .
H13 H 0.728319 0.603063 0.699314 0.072 Uiso 1 1 calc R U . . .
C14 C 0.45210(18) 0.95258(17) 0.78278(14) 0.0470(3) Uani 1 1 d . . . . .
C15 C -0.0275(3) 0.8116(3) 0.99432(18) 0.0785(6) Uani 1 1 d . . . . .
H15 H -0.111896 0.857769 1.042181 0.094 Uiso 1 1 calc R U . . .
C16 C 0.15343(16) 1.01754(15) 0.65907(14) 0.0433(3) Uani 1 1 d . . . . .
H16A H 0.077062 1.092328 0.606296 0.052 Uiso 1 1 calc R U . . .
H16B H 0.146457 1.053778 0.737154 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1956(3) 0.3978(2) 0.6163(2) 0.0725(5) Uani 1 1 d . . . . .
H17A H 0.147726 0.399221 0.542647 0.109 Uiso 1 1 calc R U . . .
H17B H 0.127458 0.396608 0.685435 0.109 Uiso 1 1 calc R U . . .
H17C H 0.285466 0.309964 0.627601 0.109 Uiso 1 1 calc R U . . .
C18 C 0.30483(19) 0.95565(17) 0.48021(13) 0.0469(3) Uani 1 1 d . . . . .
H18A H 0.407513 0.925238 0.446745 0.056 Uiso 1 1 calc R U . . .
H18B H 0.243090 1.042422 0.426301 0.056 Uiso 1 1 calc R U . . .
C19 C 0.2075(3) 0.6139(3) 0.97118(19) 0.0851(6) Uani 1 1 d . . . . .
H19 H 0.281994 0.525505 1.003984 0.102 Uiso 1 1 calc R U . . .
C20 C 0.53285(17) 0.76920(17) 0.65042(15) 0.0489(4) Uani 1 1 d . . . . .
H20 H 0.519372 0.729890 0.582657 0.059 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
F1 C14 1.3650(18) . ?
F2 C5 1.338(2) . ?
O1 C8 1.3243(18) . ?
O1 C17 1.4444(19) . ?
O2 C10 1.2046(17) . ?
O3 C8 1.1960(18) . ?
O4 C2 1.4327(19) . ?
O4 C10 1.3441(17) . ?
N1 C4 1.4201(19) . ?
N1 C16 1.4553(18) . ?
N1 C18 1.4647(17) . ?
N2 C1 1.3787(17) . ?
N2 C6 1.4187(17) . ?
N2 C16 1.4759(17) . ?
C1 C8 1.5065(18) . ?
C1 C12 1.3507(19) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C7 1.379(3) . ?
C3 C14 1.366(2) . ?
C4 C14 1.391(2) . ?
C4 C20 1.393(2) . ?
C5 C6 1.374(2) . ?
C5 C15 1.380(3) . ?
C6 C11 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C13 1.369(3) . ?
C9 H9 0.9300 . ?
C9 C15 1.375(3) . ?
C9 C19 1.365(3) . ?
C10 C12 1.4658(19) . ?
C11 H11 0.9300 . ?
C11 C19 1.376(3) . ?
C12 C18 1.5153(18) . ?
C13 H13 0.9300 . ?
C13 C20 1.378(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19 0.9300 . ?
C20 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
C8 O1 C17 115.63(13) . . ?
C10 O4 C2 116.33(13) . . ?
C4 N1 C16 115.14(11) . . ?
C4 N1 C18 115.82(12) . . ?
C16 N1 C18 108.21(11) . . ?
C1 N2 C6 120.51(11) . . ?
C1 N2 C16 115.76(11) . . ?
C6 N2 C16 118.66(11) . . ?
N2 C1 C8 114.61(11) . . ?
C12 C1 N2 121.94(12) . . ?
C12 C1 C8 123.32(12) . . ?
O4 C2 H2A 109.5 . . ?
O4 C2 H2B 109.5 . . ?
O4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C7 C3 H3 120.3 . . ?
C14 C3 H3 120.3 . . ?
C14 C3 C7 119.36(16) . . ?
C14 C4 N1 119.79(13) . . ?
C14 C4 C20 115.29(14) . . ?
C20 C4 N1 124.77(13) . . ?
F2 C5 C6 118.25(15) . . ?
F2 C5 C15 119.59(17) . . ?
C6 C5 C15 122.16(18) . . ?
C5 C6 N2 120.07(14) . . ?
C5 C6 C11 117.87(15) . . ?
C11 C6 N2 122.06(14) . . ?
C3 C7 H7 120.4 . . ?
C13 C7 C3 119.26(17) . . ?
C13 C7 H7 120.4 . . ?
O1 C8 C1 112.17(11) . . ?
O3 C8 O1 125.70(13) . . ?
O3 C8 C1 122.09(14) . . ?
C15 C9 H9 119.8 . . ?
C19 C9 H9 119.8 . . ?
C19 C9 C15 120.43(19) . . ?
O2 C10 O4 123.15(13) . . ?
O2 C10 C12 126.11(13) . . ?
O4 C10 C12 110.74(12) . . ?
C6 C11 H11 119.8 . . ?
C19 C11 C6 120.44(19) . . ?
C19 C11 H11 119.8 . . ?
C1 C12 C10 119.91(12) . . ?
C1 C12 C18 120.20(12) . . ?
C10 C12 C18 119.88(12) . . ?
C7 C13 H13 119.7 . . ?
C7 C13 C20 120.59(16) . . ?
C20 C13 H13 119.7 . . ?
F1 C14 C3 118.08(14) . . ?
F1 C14 C4 118.31(14) . . ?
C3 C14 C4 123.58(15) . . ?
C5 C15 H15 120.7 . . ?
C9 C15 C5 118.67(19) . . ?
C9 C15 H15 120.7 . . ?
N1 C16 N2 110.98(11) . . ?
N1 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
N2 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
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 . . ?
N1 C18 C12 111.68(11) . . ?
N1 C18 H18A 109.3 . . ?
N1 C18 H18B 109.3 . . ?
C12 C18 H18A 109.3 . . ?
C12 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C9 C19 C11 120.4(2) . . ?
C9 C19 H19 119.8 . . ?
C11 C19 H19 119.8 . . ?
C4 C20 H20 119.1 . . ?
C13 C20 C4 121.90(15) . . ?
C13 C20 H20 119.1 . . ?

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
F2 C5 C6 N2 0.6(2) . . . . ?
F2 C5 C6 C11 179.71(15) . . . . ?
F2 C5 C15 C9 179.62(18) . . . . ?
O2 C10 C12 C1 22.5(2) . . . . ?
O2 C10 C12 C18 -158.12(15) . . . . ?
O4 C10 C12 C1 -158.23(13) . . . . ?
O4 C10 C12 C18 21.10(18) . . . . ?
N1 C4 C14 F1 3.91(19) . . . . ?
N1 C4 C14 C3 -174.06(14) . . . . ?
N1 C4 C20 C13 173.44(14) . . . . ?
N2 C1 C8 O1 -117.99(13) . . . . ?
N2 C1 C8 O3 59.82(19) . . . . ?
N2 C1 C12 C10 -171.16(12) . . . . ?
N2 C1 C12 C18 9.5(2) . . . . ?
N2 C6 C11 C19 179.94(18) . . . . ?
C1 N2 C6 C5 -136.04(14) . . . . ?
C1 N2 C6 C11 44.9(2) . . . . ?
C1 N2 C16 N1 -42.00(16) . . . . ?
C1 C12 C18 N1 14.27(19) . . . . ?
C2 O4 C10 O2 1.3(2) . . . . ?
C2 O4 C10 C12 -177.92(14) . . . . ?
C3 C7 C13 C20 0.6(3) . . . . ?
C4 N1 C16 N2 -66.95(15) . . . . ?
C4 N1 C18 C12 81.34(15) . . . . ?
C5 C6 C11 C19 0.8(3) . . . . ?
C6 N2 C1 C8 34.11(17) . . . . ?
C6 N2 C1 C12 -150.08(13) . . . . ?
C6 N2 C16 N1 113.00(14) . . . . ?
C6 C5 C15 C9 -0.2(3) . . . . ?
C6 C11 C19 C9 -0.5(3) . . . . ?
C7 C3 C14 F1 -178.11(15) . . . . ?
C7 C3 C14 C4 -0.1(3) . . . . ?
C7 C13 C20 C4 0.9(2) . . . . ?
C8 C1 C12 C10 4.3(2) . . . . ?
C8 C1 C12 C18 -175.05(13) . . . . ?
C10 C12 C18 N1 -165.07(13) . . . . ?
C12 C1 C8 O1 66.26(17) . . . . ?
C12 C1 C8 O3 -115.93(18) . . . . ?
C14 C3 C7 C13 -1.0(3) . . . . ?
C14 C4 C20 C13 -1.9(2) . . . . ?
C15 C5 C6 N2 -179.58(16) . . . . ?
C15 C5 C6 C11 -0.5(2) . . . . ?
C15 C9 C19 C11 -0.1(4) . . . . ?
C16 N1 C4 C14 -67.05(16) . . . . ?
C16 N1 C4 C20 117.77(14) . . . . ?
C16 N1 C18 C12 -49.65(15) . . . . ?
C16 N2 C1 C8 -171.39(12) . . . . ?
C16 N2 C1 C12 4.43(19) . . . . ?
C16 N2 C6 C5 70.18(17) . . . . ?
C16 N2 C6 C11 -108.91(17) . . . . ?
C17 O1 C8 O3 4.0(2) . . . . ?
C17 O1 C8 C1 -178.24(13) . . . . ?
C18 N1 C4 C14 165.32(12) . . . . ?
C18 N1 C4 C20 -9.85(18) . . . . ?
C18 N1 C16 N2 64.41(14) . . . . ?
C19 C9 C15 C5 0.5(3) . . . . ?
C20 C4 C14 F1 179.52(12) . . . . ?
C20 C4 C14 C3 1.6(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_230227hzs3cf3_0m
_database_code_depnum_ccdc_archive 'CCDC 2353767'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F6 N2 O4'
_chemical_formula_sum            'C22 H18 F6 N2 O4'
_chemical_formula_weight         488.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   16.285(2)
_cell_length_b                   11.5946(14)
_cell_length_c                   24.451(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.365(2)
_cell_angle_gamma                90
_cell_volume                     4355.6(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3935
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.919
_cell_measurement_theta_min      2.530
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.9033.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21631
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.327
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4905
_reflns_number_total             7651
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         7651
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+9.5133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2290
_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. Rigid body (RIGU) restrains
 F1, F1A, F2, F2A, F6, F6A, F7, F7A, F8, F8A, F10, F10A, C5, C21, F3, F3A, F4,
 F4A, F5, F5A, F9, F9A, F11, F11A, F12, F12A, C37, C43
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F2A)=Sof(F6A)=Sof(F7A)=1-FVAR(1)
 Sof(F2)=Sof(F6)=Sof(F7)=FVAR(1)
 Sof(F1A)=Sof(F8A)=Sof(F10A)=1-FVAR(2)
 Sof(F1)=Sof(F8)=Sof(F10)=FVAR(2)
 Sof(F5A)=Sof(F9A)=Sof(F12A)=1-FVAR(3)
 Sof(F5)=Sof(F9)=Sof(F12)=FVAR(3)
 Sof(F3A)=Sof(F4A)=Sof(F11A)=1-FVAR(4)
 Sof(F3)=Sof(F4)=Sof(F11)=FVAR(4)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C38(H38A,H38B), C22(H22A,H22B), C28(H28A,H28B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C24(H24), C29(H29), C33(H33), C35(H35), C36(H36), C40(H40),
 C13(H13), C17(H17), C27(H27), C30(H30), C31(H31), C39(H39), C42(H42), C44(H44)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C9(H9A,H9B,H9C), C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2790(5) 0.3662(11) 0.5210(5) 0.097(4) Uani 0.64(2) 1 d . . P A 1
F1A F 0.304(3) 0.435(4) 0.5179(10) 0.206(16) Uani 0.36(2) 1 d . . P A 2
F2 F 0.6896(10) 0.8533(16) 1.0183(5) 0.149(7) Uani 0.571(15) 1 d . . P B 1
F2A F 0.7042(14) 0.918(2) 0.9928(7) 0.147(9) Uani 0.429(15) 1 d . . P B 2
F6 F 0.5609(10) 0.8421(14) 0.9875(6) 0.117(5) Uani 0.571(15) 1 d . . P B 1
F6A F 0.6571(12) 0.7646(16) 1.0166(5) 0.130(6) Uani 0.429(15) 1 d . . P B 2
F7 F 0.6217(10) 0.9773(7) 0.9612(4) 0.108(4) Uani 0.571(15) 1 d . . P B 1
F7A F 0.5622(15) 0.893(2) 0.9678(10) 0.165(12) Uani 0.429(15) 1 d . . P B 2
F8 F 0.3734(11) 0.2917(15) 0.4921(5) 0.136(6) Uani 0.64(2) 1 d . . P A 1
F8A F 0.337(2) 0.274(3) 0.5012(13) 0.189(14) Uani 0.36(2) 1 d . . P A 2
F10 F 0.3770(10) 0.4702(11) 0.5113(4) 0.115(5) Uani 0.64(2) 1 d . . P A 1
F10A F 0.4207(16) 0.405(4) 0.5031(7) 0.142(11) Uani 0.36(2) 1 d . . P A 2
O4 O 0.27380(19) 0.5753(3) 0.85317(13) 0.0459(8) Uani 1 1 d . . . . .
O5 O 0.2298(2) 0.4801(3) 0.66098(13) 0.0507(9) Uani 1 1 d . . . . .
O6 O 0.19373(19) 0.4948(3) 0.76900(14) 0.0542(9) Uani 1 1 d . . . . .
O7 O 0.2621(2) 0.3090(3) 0.70572(16) 0.0599(10) Uani 1 1 d . . . . .
N2 N 0.4328(2) 0.4564(3) 0.73622(16) 0.0410(9) Uani 1 1 d . . . . .
N4 N 0.4930(2) 0.5978(3) 0.80927(15) 0.0380(9) Uani 1 1 d . . . . .
C3 C 0.5123(3) 0.3063(4) 0.7054(2) 0.0506(12) Uani 1 1 d . . . . .
H3 H 0.544810 0.292787 0.743972 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3648(5) 0.3666(7) 0.5293(3) 0.0760(17) Uani 1 1 d . . . . .
C6 C 0.5654(3) 0.6630(4) 0.84159(19) 0.0386(10) Uani 1 1 d . . . . .
C7 C 0.7064(3) 0.7457(5) 0.8525(3) 0.0596(15) Uani 1 1 d . . . . .
H7 H 0.753636 0.752891 0.839431 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3455(3) 0.5292(4) 0.78936(18) 0.0342(10) Uani 1 1 d . . . . .
C10 C 0.3534(3) 0.4703(4) 0.74394(18) 0.0367(10) Uani 1 1 d . . . . .
C11 C 0.4156(3) 0.3436(5) 0.5910(2) 0.0495(12) Uani 1 1 d . . . . .
C15 C 0.1959(3) 0.5866(6) 0.8689(2) 0.0635(16) Uani 1 1 d . . . . .
H15A H 0.156457 0.639445 0.842869 0.095 Uiso 1 1 calc R U . . .
H15B H 0.211138 0.615316 0.907854 0.095 Uiso 1 1 calc R U . . .
H15C H 0.168436 0.512654 0.866472 0.095 Uiso 1 1 calc R U . . .
C16 C 0.4204(3) 0.5926(4) 0.83133(19) 0.0390(10) Uani 1 1 d . . . . .
H16A H 0.402384 0.670088 0.837021 0.047 Uiso 1 1 calc R U . . .
H16B H 0.438449 0.553380 0.868482 0.047 Uiso 1 1 calc R U . . .
C18 C 0.2628(3) 0.5305(4) 0.80073(19) 0.0390(10) Uani 1 1 d . . . . .
C19 C 0.1522(3) 0.4306(6) 0.6198(2) 0.0750(18) Uani 1 1 d . . . . .
H19A H 0.124807 0.486557 0.590477 0.112 Uiso 1 1 calc R U . . .
H19B H 0.112548 0.408545 0.639567 0.112 Uiso 1 1 calc R U . . .
H19C H 0.167658 0.363935 0.602098 0.112 Uiso 1 1 calc R U . . .
C21 C 0.6318(5) 0.8579(7) 0.9722(3) 0.0801(18) Uani 1 1 d . . . . .
C23 C 0.6364(3) 0.7920(5) 0.9208(2) 0.0523(13) Uani 1 1 d . . . . .
C24 C 0.5663(3) 0.7221(4) 0.89143(19) 0.0453(12) Uani 1 1 d . . . . .
H24 H 0.519583 0.714768 0.905097 0.054 Uiso 1 1 calc R U . . .
C26 C 0.4466(3) 0.3894(4) 0.69141(18) 0.0380(10) Uani 1 1 d . . . . .
C29 C 0.7067(3) 0.8038(5) 0.9018(2) 0.0591(15) Uani 1 1 d . . . . .
H29 H 0.753609 0.850235 0.921847 0.071 Uiso 1 1 calc R U . . .
C33 C 0.4803(4) 0.2625(5) 0.6048(2) 0.0615(15) Uani 1 1 d . . . . .
H33 H 0.491357 0.219986 0.575712 0.074 Uiso 1 1 calc R U . . .
C34 C 0.2764(3) 0.4089(5) 0.7022(2) 0.0422(11) Uani 1 1 d . . . . .
C35 C 0.5294(4) 0.2441(5) 0.6624(2) 0.0608(15) Uani 1 1 d . . . . .
H35 H 0.573851 0.189678 0.671971 0.073 Uiso 1 1 calc R U . . .
C36 C 0.6374(3) 0.6775(5) 0.8226(2) 0.0494(12) Uani 1 1 d . . . . .
H36 H 0.638210 0.640077 0.789153 0.059 Uiso 1 1 calc R U . . .
C38 C 0.5086(3) 0.4880(4) 0.7859(2) 0.0429(11) Uani 1 1 d . . . . .
H38A H 0.519531 0.428911 0.815511 0.052 Uiso 1 1 calc R U . . .
H38B H 0.559582 0.493841 0.773859 0.052 Uiso 1 1 calc R U . . .
C40 C 0.3988(3) 0.4080(4) 0.6338(2) 0.0452(11) Uani 1 1 d . . . . .
H40 H 0.355248 0.463699 0.623813 0.054 Uiso 1 1 calc R U . . .
F3 F 0.5854(15) 0.2469(16) 0.4915(7) 0.128(6) Uani 0.46(2) 1 d . . P C 1
F3A F 0.5059(12) 0.1348(18) 0.4750(11) 0.112(5) Uani 0.54(2) 1 d . . P C 2
F4 F 0.525(2) 0.086(3) 0.4757(12) 0.177(12) Uani 0.46(2) 1 d . . P C 1
F4A F 0.6054(16) 0.0225(17) 0.4807(6) 0.134(7) Uani 0.54(2) 1 d . . P C 2
F5 F 0.4060(14) -0.3209(19) -0.0251(4) 0.142(8) Uani 0.52(2) 1 d . . P D 1
F5A F 0.4547(11) -0.3870(19) -0.0106(7) 0.127(7) Uani 0.48(2) 1 d . . P D 2
F9 F 0.4270(12) -0.4699(12) 0.0210(7) 0.134(7) Uani 0.52(2) 1 d . . P D 1
F9A F 0.3744(19) -0.444(2) 0.0341(7) 0.171(11) Uani 0.48(2) 1 d . . P D 2
F11 F 0.6608(13) 0.101(2) 0.4938(5) 0.130(8) Uani 0.46(2) 1 d . . P C 1
F11A F 0.6288(18) 0.202(3) 0.5035(7) 0.197(12) Uani 0.54(2) 1 d . . P C 2
F12 F 0.3227(6) -0.3664(15) 0.0182(6) 0.099(5) Uani 0.52(2) 1 d . . P D 1
F12A F 0.3523(15) -0.2880(17) -0.0118(6) 0.150(10) Uani 0.48(2) 1 d . . P D 2
O1 O 0.16878(18) -0.0775(3) 0.14509(13) 0.0473(8) Uani 1 1 d . . . . .
O2 O 0.1741(2) 0.0114(3) 0.22741(14) 0.0557(9) Uani 1 1 d . . . . .
O3 O 0.3079(2) 0.1931(3) 0.29110(16) 0.0584(9) Uani 1 1 d . . . . .
O8 O 0.3173(2) 0.0219(3) 0.33583(13) 0.0490(8) Uani 1 1 d . . . . .
N1 N 0.4317(2) -0.1022(3) 0.18811(15) 0.0384(9) Uani 1 1 d . . . . .
N3 N 0.4456(2) 0.0419(3) 0.25973(15) 0.0387(9) Uani 1 1 d . . . . .
C1 C 0.3584(3) 0.0289(4) 0.25265(18) 0.0331(9) Uani 1 1 d . . . . .
C2 C 0.5724(3) 0.1575(5) 0.4038(2) 0.0541(13) Uani 1 1 d . . . . .
C4 C 0.3047(3) -0.0302(4) 0.20759(18) 0.0340(10) Uani 1 1 d . . . . .
C9 C 0.0756(3) -0.0875(6) 0.1301(2) 0.0646(16) Uani 1 1 d . . . . .
H9A H 0.052402 -0.128105 0.094078 0.097 Uiso 1 1 calc R U . . .
H9B H 0.050316 -0.011864 0.126339 0.097 Uiso 1 1 calc R U . . .
H9C H 0.062221 -0.129048 0.160063 0.097 Uiso 1 1 calc R U . . .
C12 C 0.5045(3) 0.1092(4) 0.30413(19) 0.0391(10) Uani 1 1 d . . . . .
C13 C 0.5572(3) 0.1896(4) 0.2898(2) 0.0488(12) Uani 1 1 d . . . . .
H13 H 0.551919 0.200793 0.251069 0.059 Uiso 1 1 calc R U . . .
C14 C 0.2113(3) -0.0291(4) 0.19646(19) 0.0390(10) Uani 1 1 d . . . . .
C17 C 0.6169(3) 0.2528(5) 0.3320(3) 0.0630(15) Uani 1 1 d . . . . .
H17 H 0.651949 0.306059 0.321764 0.076 Uiso 1 1 calc R U . . .
C20 C 0.4717(3) -0.1692(4) 0.15563(18) 0.0382(10) Uani 1 1 d . . . . .
C22 C 0.4711(3) 0.0075(4) 0.2103(2) 0.0415(11) Uani 1 1 d . . . . .
H22A H 0.452455 0.065589 0.180171 0.050 Uiso 1 1 calc R U . . .
H22B H 0.533948 0.001104 0.222105 0.050 Uiso 1 1 calc R U . . .
C25 C 0.4627(3) -0.2976(4) 0.0761(2) 0.0485(12) Uani 1 1 d . . . . .
C27 C 0.5624(3) -0.1854(5) 0.1754(2) 0.0495(12) Uani 1 1 d . . . . .
H27 H 0.596733 -0.149088 0.209136 0.059 Uiso 1 1 calc R U . . .
C28 C 0.3375(3) -0.0955(4) 0.16586(18) 0.0377(10) Uani 1 1 d . . . . .
H28A H 0.313025 -0.172603 0.160387 0.045 Uiso 1 1 calc R U . . .
H28B H 0.319040 -0.056789 0.128571 0.045 Uiso 1 1 calc R U . . .
C30 C 0.4227(3) -0.2265(4) 0.10511(19) 0.0443(11) Uani 1 1 d . . . . .
H30 H 0.362600 -0.216731 0.090849 0.053 Uiso 1 1 calc R U . . .
C31 C 0.5517(4) -0.3121(5) 0.0956(2) 0.0555(14) Uani 1 1 d . . . . .
H31 H 0.578183 -0.359783 0.075798 0.067 Uiso 1 1 calc R U . . .
C32 C 0.3242(3) 0.0925(5) 0.29472(19) 0.0414(11) Uani 1 1 d . . . . .
C37 C 0.4071(5) -0.3606(7) 0.0231(3) 0.0721(16) Uani 1 1 d . . . . .
C39 C 0.6253(3) 0.2377(5) 0.3896(3) 0.0642(15) Uani 1 1 d . . . . .
H39 H 0.665570 0.280517 0.418352 0.077 Uiso 1 1 calc R U . . .
C41 C 0.2815(4) 0.0732(6) 0.3763(2) 0.0734(18) Uani 1 1 d . . . . .
H41A H 0.223998 0.101455 0.355951 0.110 Uiso 1 1 calc R U . . .
H41B H 0.317804 0.136039 0.395836 0.110 Uiso 1 1 calc R U . . .
H41C H 0.278581 0.016514 0.404228 0.110 Uiso 1 1 calc R U . . .
C42 C 0.6008(3) -0.2550(5) 0.1450(2) 0.0545(13) Uani 1 1 d . . . . .
H42 H 0.660966 -0.263376 0.158026 0.065 Uiso 1 1 calc R U . . .
C43 C 0.5831(5) 0.1391(8) 0.4658(3) 0.0826(18) Uani 1 1 d . . . . .
C44 C 0.5136(3) 0.0925(4) 0.36183(19) 0.0444(11) Uani 1 1 d . . . . .
H44 H 0.479966 0.037431 0.372189 0.053 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
F1 C5 1.344(11) . ?
F1A C5 1.22(2) . ?
F2 C21 1.206(10) . ?
F2A C21 1.315(13) . ?
F6 C21 1.338(14) . ?
F6A C21 1.491(17) . ?
F7 C21 1.410(11) . ?
F7A C21 1.18(2) . ?
F8 C5 1.299(12) . ?
F8A C5 1.28(3) . ?
F10 C5 1.317(11) . ?
F10A C5 1.349(18) . ?
O4 C15 1.449(5) . ?
O4 C18 1.340(5) . ?
O5 C19 1.448(6) . ?
O5 C34 1.329(6) . ?
O6 C18 1.208(5) . ?
O7 C34 1.190(6) . ?
N2 C10 1.377(5) . ?
N2 C26 1.420(5) . ?
N2 C38 1.463(6) . ?
N4 C6 1.403(5) . ?
N4 C16 1.454(5) . ?
N4 C38 1.453(6) . ?
C3 H3 0.9300 . ?
C3 C26 1.396(6) . ?
C3 C35 1.377(7) . ?
C5 C11 1.484(8) . ?
C6 C24 1.394(6) . ?
C6 C36 1.406(6) . ?
C7 H7 0.9300 . ?
C7 C29 1.379(8) . ?
C7 C36 1.370(7) . ?
C8 C10 1.345(6) . ?
C8 C16 1.500(6) . ?
C8 C18 1.463(6) . ?
C10 C34 1.507(6) . ?
C11 C33 1.369(7) . ?
C11 C40 1.386(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C23 1.493(9) . ?
C23 C24 1.391(7) . ?
C23 C29 1.378(7) . ?
C24 H24 0.9300 . ?
C26 C40 1.381(6) . ?
C29 H29 0.9300 . ?
C33 H33 0.9300 . ?
C33 C35 1.385(8) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C40 H40 0.9300 . ?
F3 C43 1.393(17) . ?
F3A C43 1.350(17) . ?
F4 C43 1.21(2) . ?
F4A C43 1.416(16) . ?
F5 C37 1.259(12) . ?
F5A C37 1.340(13) . ?
F9 C37 1.313(13) . ?
F9A C37 1.182(15) . ?
F11 C43 1.299(14) . ?
F11A C43 1.219(16) . ?
F12 C37 1.341(11) . ?
F12A C37 1.314(13) . ?
O1 C9 1.442(5) . ?
O1 C14 1.340(5) . ?
O2 C14 1.211(5) . ?
O3 C32 1.194(6) . ?
O8 C32 1.330(6) . ?
O8 C41 1.434(6) . ?
N1 C20 1.415(5) . ?
N1 C22 1.447(6) . ?
N1 C28 1.450(5) . ?
N3 C1 1.382(5) . ?
N3 C12 1.420(5) . ?
N3 C22 1.457(5) . ?
C1 C4 1.345(6) . ?
C1 C32 1.514(6) . ?
C2 C39 1.387(8) . ?
C2 C43 1.481(8) . ?
C2 C44 1.374(7) . ?
C4 C14 1.453(6) . ?
C4 C28 1.503(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C13 1.389(6) . ?
C12 C44 1.382(6) . ?
C13 H13 0.9300 . ?
C13 C17 1.372(7) . ?
C17 H17 0.9300 . ?
C17 C39 1.381(8) . ?
C20 C27 1.407(6) . ?
C20 C30 1.396(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C25 C30 1.384(6) . ?
C25 C31 1.377(7) . ?
C25 C37 1.502(8) . ?
C27 H27 0.9300 . ?
C27 C42 1.379(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C42 1.376(7) . ?
C39 H39 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42 0.9300 . ?
C44 H44 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 C15 116.0(4) . . ?
C34 O5 C19 115.4(4) . . ?
C10 N2 C26 124.5(4) . . ?
C10 N2 C38 115.5(3) . . ?
C26 N2 C38 118.1(3) . . ?
C6 N4 C16 116.7(3) . . ?
C6 N4 C38 118.0(3) . . ?
C38 N4 C16 112.3(3) . . ?
C26 C3 H3 119.7 . . ?
C35 C3 H3 119.7 . . ?
C35 C3 C26 120.5(5) . . ?
F1 C5 C11 110.8(7) . . ?
F1A C5 F8A 108(3) . . ?
F1A C5 F10A 107.4(19) . . ?
F1A C5 C11 119.0(12) . . ?
F8 C5 F1 103.9(10) . . ?
F8 C5 F10 108.2(10) . . ?
F8 C5 C11 116.0(8) . . ?
F8A C5 F10A 101.3(16) . . ?
F8A C5 C11 112.0(18) . . ?
F10 C5 F1 102.6(9) . . ?
F10 C5 C11 114.1(7) . . ?
F10A C5 C11 107.7(10) . . ?
N4 C6 C36 121.1(4) . . ?
C24 C6 N4 121.3(4) . . ?
C24 C6 C36 117.5(4) . . ?
C29 C7 H7 119.6 . . ?
C36 C7 H7 119.6 . . ?
C36 C7 C29 120.9(5) . . ?
C10 C8 C16 122.4(4) . . ?
C10 C8 C18 120.5(4) . . ?
C18 C8 C16 117.1(4) . . ?
N2 C10 C34 117.4(4) . . ?
C8 C10 N2 121.5(4) . . ?
C8 C10 C34 120.9(4) . . ?
C33 C11 C5 120.0(5) . . ?
C33 C11 C40 120.8(5) . . ?
C40 C11 C5 119.2(5) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C8 110.1(3) . . ?
N4 C16 H16A 109.6 . . ?
N4 C16 H16B 109.6 . . ?
C8 C16 H16A 109.6 . . ?
C8 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
O4 C18 C8 110.3(4) . . ?
O6 C18 O4 123.2(4) . . ?
O6 C18 C8 126.5(4) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F2 C21 F6 102.3(12) . . ?
F2 C21 F7 103.1(10) . . ?
F2 C21 C23 121.4(9) . . ?
F2A C21 F6A 96.1(12) . . ?
F2A C21 C23 107.6(9) . . ?
F6 C21 F7 97.6(10) . . ?
F6 C21 C23 117.0(8) . . ?
F6A C21 C23 99.3(8) . . ?
F7 C21 C23 112.1(6) . . ?
F7A C21 F2A 124.4(17) . . ?
F7A C21 F6A 110.2(17) . . ?
F7A C21 C23 114.7(11) . . ?
C24 C23 C21 118.1(5) . . ?
C29 C23 C21 120.9(5) . . ?
C29 C23 C24 121.0(5) . . ?
C6 C24 H24 119.8 . . ?
C23 C24 C6 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C3 C26 N2 119.6(4) . . ?
C40 C26 N2 121.4(4) . . ?
C40 C26 C3 118.9(4) . . ?
C7 C29 H29 120.5 . . ?
C23 C29 C7 118.9(5) . . ?
C23 C29 H29 120.5 . . ?
C11 C33 H33 120.2 . . ?
C11 C33 C35 119.6(5) . . ?
C35 C33 H33 120.2 . . ?
O5 C34 C10 111.0(4) . . ?
O7 C34 O5 125.7(5) . . ?
O7 C34 C10 123.3(4) . . ?
C3 C35 C33 120.1(5) . . ?
C3 C35 H35 120.0 . . ?
C33 C35 H35 120.0 . . ?
C6 C36 H36 119.4 . . ?
C7 C36 C6 121.2(5) . . ?
C7 C36 H36 119.4 . . ?
N2 C38 H38A 109.7 . . ?
N2 C38 H38B 109.7 . . ?
N4 C38 N2 109.7(4) . . ?
N4 C38 H38A 109.7 . . ?
N4 C38 H38B 109.7 . . ?
H38A C38 H38B 108.2 . . ?
C11 C40 H40 120.0 . . ?
C26 C40 C11 120.0(5) . . ?
C26 C40 H40 120.0 . . ?
C14 O1 C9 116.4(4) . . ?
C32 O8 C41 114.9(4) . . ?
C20 N1 C22 117.6(3) . . ?
C20 N1 C28 116.5(3) . . ?
C22 N1 C28 112.1(3) . . ?
C1 N3 C12 124.1(4) . . ?
C1 N3 C22 115.5(3) . . ?
C12 N3 C22 118.6(3) . . ?
N3 C1 C32 117.2(4) . . ?
C4 C1 N3 121.4(4) . . ?
C4 C1 C32 121.3(4) . . ?
C39 C2 C43 118.7(5) . . ?
C44 C2 C39 121.1(5) . . ?
C44 C2 C43 120.1(5) . . ?
C1 C4 C14 120.3(4) . . ?
C1 C4 C28 122.1(4) . . ?
C14 C4 C28 117.5(4) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C12 N3 119.5(4) . . ?
C44 C12 N3 121.3(4) . . ?
C44 C12 C13 119.1(4) . . ?
C12 C13 H13 119.6 . . ?
C17 C13 C12 120.7(5) . . ?
C17 C13 H13 119.6 . . ?
O1 C14 C4 110.9(4) . . ?
O2 C14 O1 122.5(4) . . ?
O2 C14 C4 126.6(4) . . ?
C13 C17 H17 119.8 . . ?
C13 C17 C39 120.4(5) . . ?
C39 C17 H17 119.8 . . ?
C27 C20 N1 120.5(4) . . ?
C30 C20 N1 121.5(4) . . ?
C30 C20 C27 117.9(4) . . ?
N1 C22 N3 109.8(3) . . ?
N1 C22 H22A 109.7 . . ?
N1 C22 H22B 109.7 . . ?
N3 C22 H22A 109.7 . . ?
N3 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C30 C25 C37 118.7(5) . . ?
C31 C25 C30 121.1(5) . . ?
C31 C25 C37 120.2(5) . . ?
C20 C27 H27 119.8 . . ?
C42 C27 C20 120.3(5) . . ?
C42 C27 H27 119.8 . . ?
N1 C28 C4 110.0(3) . . ?
N1 C28 H28A 109.7 . . ?
N1 C28 H28B 109.7 . . ?
C4 C28 H28A 109.7 . . ?
C4 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C20 C30 H30 119.7 . . ?
C25 C30 C20 120.5(4) . . ?
C25 C30 H30 119.7 . . ?
C25 C31 H31 120.6 . . ?
C42 C31 C25 118.9(4) . . ?
C42 C31 H31 120.6 . . ?
O3 C32 O8 125.8(4) . . ?
O3 C32 C1 123.3(4) . . ?
O8 C32 C1 110.9(4) . . ?
F5 C37 F9 104.1(11) . . ?
F5 C37 F12 103.8(10) . . ?
F5 C37 C25 116.6(9) . . ?
F5A C37 C25 109.7(9) . . ?
F9 C37 F12 101.9(11) . . ?
F9 C37 C25 114.7(8) . . ?
F9A C37 F5A 110.4(14) . . ?
F9A C37 F12A 114.4(16) . . ?
F9A C37 C25 113.1(10) . . ?
F12 C37 C25 114.1(6) . . ?
F12A C37 F5A 98.9(11) . . ?
F12A C37 C25 109.5(8) . . ?
C2 C39 H39 120.6 . . ?
C17 C39 C2 118.8(5) . . ?
C17 C39 H39 120.6 . . ?
O8 C41 H41A 109.5 . . ?
O8 C41 H41B 109.5 . . ?
O8 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C27 C42 H42 119.4 . . ?
C31 C42 C27 121.3(5) . . ?
C31 C42 H42 119.4 . . ?
F3 C43 C2 107.9(10) . . ?
F3A C43 F4A 95.5(12) . . ?
F3A C43 C2 112.1(12) . . ?
F4 C43 F3 105.5(18) . . ?
F4 C43 F11 114.3(18) . . ?
F4 C43 C2 116.2(14) . . ?
F4A C43 C2 109.5(8) . . ?
F11 C43 F3 100.8(11) . . ?
F11 C43 C2 110.6(9) . . ?
F11A C43 F3A 105.4(17) . . ?
F11A C43 F4A 109.8(13) . . ?
F11A C43 C2 121.5(12) . . ?
C2 C44 C12 119.9(5) . . ?
C2 C44 H44 120.0 . . ?
C12 C44 H44 120.0 . . ?

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
F1 C5 C11 C33 131.3(8) . . . . ?
F1 C5 C11 C40 -51.0(10) . . . . ?
F1A C5 C11 C33 176(3) . . . . ?
F1A C5 C11 C40 -6(3) . . . . ?
F2 C21 C23 C24 128.1(15) . . . . ?
F2 C21 C23 C29 -54.4(16) . . . . ?
F2A C21 C23 C24 -179.8(14) . . . . ?
F2A C21 C23 C29 -2.4(16) . . . . ?
F6 C21 C23 C24 2.0(13) . . . . ?
F6 C21 C23 C29 179.4(11) . . . . ?
F6A C21 C23 C24 80.7(9) . . . . ?
F6A C21 C23 C29 -101.9(9) . . . . ?
F7 C21 C23 C24 -109.5(9) . . . . ?
F7 C21 C23 C29 67.9(11) . . . . ?
F7A C21 C23 C24 -37(2) . . . . ?
F7A C21 C23 C29 140.6(19) . . . . ?
F8 C5 C11 C33 13.3(14) . . . . ?
F8 C5 C11 C40 -169.1(12) . . . . ?
F8A C5 C11 C33 49(2) . . . . ?
F8A C5 C11 C40 -133(2) . . . . ?
F10 C5 C11 C33 -113.5(11) . . . . ?
F10 C5 C11 C40 64.1(12) . . . . ?
F10A C5 C11 C33 -61(2) . . . . ?
F10A C5 C11 C40 116(2) . . . . ?
N2 C10 C34 O5 -99.1(5) . . . . ?
N2 C10 C34 O7 79.0(6) . . . . ?
N2 C26 C40 C11 178.0(4) . . . . ?
N4 C6 C24 C23 -176.0(4) . . . . ?
N4 C6 C36 C7 176.7(5) . . . . ?
C3 C26 C40 C11 0.8(7) . . . . ?
C5 C11 C33 C35 177.9(6) . . . . ?
C5 C11 C40 C26 -178.7(5) . . . . ?
C6 N4 C16 C8 174.9(4) . . . . ?
C6 N4 C38 N2 -157.0(4) . . . . ?
C8 C10 C34 O5 85.8(5) . . . . ?
C8 C10 C34 O7 -96.2(6) . . . . ?
C10 N2 C26 C3 -128.5(5) . . . . ?
C10 N2 C26 C40 54.2(6) . . . . ?
C10 N2 C38 N4 -45.4(5) . . . . ?
C10 C8 C16 N4 10.6(6) . . . . ?
C10 C8 C18 O4 168.6(4) . . . . ?
C10 C8 C18 O6 -10.0(7) . . . . ?
C11 C33 C35 C3 0.7(9) . . . . ?
C15 O4 C18 O6 -4.1(7) . . . . ?
C15 O4 C18 C8 177.3(4) . . . . ?
C16 N4 C6 C24 -1.8(6) . . . . ?
C16 N4 C6 C36 -177.3(4) . . . . ?
C16 N4 C38 N2 62.9(5) . . . . ?
C16 C8 C10 N2 5.8(7) . . . . ?
C16 C8 C10 C34 -179.2(4) . . . . ?
C16 C8 C18 O4 -9.6(6) . . . . ?
C16 C8 C18 O6 171.9(5) . . . . ?
C18 C8 C10 N2 -172.2(4) . . . . ?
C18 C8 C10 C34 2.8(7) . . . . ?
C18 C8 C16 N4 -171.3(4) . . . . ?
C19 O5 C34 O7 4.4(7) . . . . ?
C19 O5 C34 C10 -177.7(4) . . . . ?
C21 C23 C24 C6 177.0(5) . . . . ?
C21 C23 C29 C7 -176.9(6) . . . . ?
C24 C6 C36 C7 1.0(7) . . . . ?
C24 C23 C29 C7 0.5(8) . . . . ?
C26 N2 C10 C8 175.9(4) . . . . ?
C26 N2 C10 C34 0.7(6) . . . . ?
C26 N2 C38 N4 149.8(4) . . . . ?
C26 C3 C35 C33 -1.0(8) . . . . ?
C29 C7 C36 C6 -1.0(8) . . . . ?
C29 C23 C24 C6 -0.5(7) . . . . ?
C33 C11 C40 C26 -1.1(8) . . . . ?
C35 C3 C26 N2 -177.1(5) . . . . ?
C35 C3 C26 C40 0.2(7) . . . . ?
C36 C6 C24 C23 -0.3(7) . . . . ?
C36 C7 C29 C23 0.2(8) . . . . ?
C38 N2 C10 C8 12.2(6) . . . . ?
C38 N2 C10 C34 -163.0(4) . . . . ?
C38 N2 C26 C3 34.8(6) . . . . ?
C38 N2 C26 C40 -142.5(4) . . . . ?
C38 N4 C6 C24 -140.2(4) . . . . ?
C38 N4 C6 C36 44.3(6) . . . . ?
C38 N4 C16 C8 -44.5(5) . . . . ?
C40 C11 C33 C35 0.3(8) . . . . ?
N1 C20 C27 C42 177.1(4) . . . . ?
N1 C20 C30 C25 -175.7(4) . . . . ?
N3 C1 C4 C14 -171.4(4) . . . . ?
N3 C1 C4 C28 6.3(6) . . . . ?
N3 C1 C32 O3 78.1(6) . . . . ?
N3 C1 C32 O8 -100.4(4) . . . . ?
N3 C12 C13 C17 -177.6(5) . . . . ?
N3 C12 C44 C2 178.7(4) . . . . ?
C1 N3 C12 C13 -129.8(5) . . . . ?
C1 N3 C12 C44 53.4(6) . . . . ?
C1 N3 C22 N1 -45.2(5) . . . . ?
C1 C4 C14 O1 170.3(4) . . . . ?
C1 C4 C14 O2 -8.0(7) . . . . ?
C1 C4 C28 N1 10.9(6) . . . . ?
C4 C1 C32 O3 -96.8(6) . . . . ?
C4 C1 C32 O8 84.7(5) . . . . ?
C9 O1 C14 O2 -4.8(7) . . . . ?
C9 O1 C14 C4 176.8(4) . . . . ?
C12 N3 C1 C4 175.8(4) . . . . ?
C12 N3 C1 C32 0.9(6) . . . . ?
C12 N3 C22 N1 149.4(4) . . . . ?
C12 C13 C17 C39 -0.3(8) . . . . ?
C13 C12 C44 C2 1.8(7) . . . . ?
C13 C17 C39 C2 0.2(9) . . . . ?
C14 C4 C28 N1 -171.3(4) . . . . ?
C20 N1 C22 N3 -157.3(4) . . . . ?
C20 N1 C28 C4 175.2(4) . . . . ?
C20 C27 C42 C31 -1.6(8) . . . . ?
C22 N1 C20 C27 45.9(6) . . . . ?
C22 N1 C20 C30 -137.8(4) . . . . ?
C22 N1 C28 C4 -45.3(5) . . . . ?
C22 N3 C1 C4 11.3(6) . . . . ?
C22 N3 C1 C32 -163.6(4) . . . . ?
C22 N3 C12 C13 34.3(6) . . . . ?
C22 N3 C12 C44 -142.6(4) . . . . ?
C25 C31 C42 C27 1.1(8) . . . . ?
C27 C20 C30 C25 0.6(7) . . . . ?
C28 N1 C20 C27 -176.8(4) . . . . ?
C28 N1 C20 C30 -0.6(6) . . . . ?
C28 N1 C22 N3 63.6(5) . . . . ?
C28 C4 C14 O1 -7.5(6) . . . . ?
C28 C4 C14 O2 174.2(5) . . . . ?
C30 C20 C27 C42 0.7(7) . . . . ?
C30 C25 C31 C42 0.3(8) . . . . ?
C30 C25 C37 F5 103.6(15) . . . . ?
C30 C25 C37 F5A 156.3(12) . . . . ?
C30 C25 C37 F9 -134.5(14) . . . . ?
C30 C25 C37 F9A -80(2) . . . . ?
C30 C25 C37 F12 -17.5(13) . . . . ?
C30 C25 C37 F12A 48.8(17) . . . . ?
C31 C25 C30 C20 -1.1(7) . . . . ?
C31 C25 C37 F5 -77.4(16) . . . . ?
C31 C25 C37 F5A -24.6(14) . . . . ?
C31 C25 C37 F9 44.6(15) . . . . ?
C31 C25 C37 F9A 99(2) . . . . ?
C31 C25 C37 F12 161.6(11) . . . . ?
C31 C25 C37 F12A -132.1(16) . . . . ?
C32 C1 C4 C14 3.3(6) . . . . ?
C32 C1 C4 C28 -179.0(4) . . . . ?
C37 C25 C30 C20 178.0(5) . . . . ?
C37 C25 C31 C42 -178.8(6) . . . . ?
C39 C2 C43 F3 47.6(13) . . . . ?
C39 C2 C43 F3A 135.1(11) . . . . ?
C39 C2 C43 F4 166(2) . . . . ?
C39 C2 C43 F4A -120.2(13) . . . . ?
C39 C2 C43 F11 -61.8(17) . . . . ?
C39 C2 C43 F11A 9(2) . . . . ?
C39 C2 C44 C12 -2.0(8) . . . . ?
C41 O8 C32 O3 4.3(7) . . . . ?
C41 O8 C32 C1 -177.2(4) . . . . ?
C43 C2 C39 C17 178.3(6) . . . . ?
C43 C2 C44 C12 -179.3(5) . . . . ?
C44 C2 C39 C17 1.0(8) . . . . ?
C44 C2 C43 F3 -135.1(11) . . . . ?
C44 C2 C43 F3A -47.6(13) . . . . ?
C44 C2 C43 F4 -17(2) . . . . ?
C44 C2 C43 F4A 57.1(14) . . . . ?
C44 C2 C43 F11 115.5(16) . . . . ?
C44 C2 C43 F11A -173(2) . . . . ?
C44 C12 C13 C17 -0.7(7) . . . . ?

_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_hzs-1
_database_code_depnum_ccdc_archive 'CCDC 2353617'
loop_
_audit_author_name
_audit_author_address
'Zeshenghuang Zeshenghuang'
;Southern Medical University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-08-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C32 H28 N2 O4)'
_chemical_formula_sum            'C64 H56 N4 O8'
_chemical_formula_weight         1009.12
_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                   9.5517(6)
_cell_length_b                   11.8115(7)
_cell_length_c                   23.1264(12)
_cell_angle_alpha                83.899(5)
_cell_angle_beta                 85.964(5)
_cell_angle_gamma                89.561(5)
_cell_volume                     2587.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5354
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.3050
_cell_measurement_theta_min      3.7950
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24656
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.127
_diffrn_reflns_theta_min         3.764
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  45.00   0.50    0.50    --   41.60 -82.00 -60.00  156
  2  ω    -45.00  56.00   0.50    0.50    --   41.60 -77.00 150.00  202
  3  ω    -39.00  44.00   0.50    0.50    --   41.60 -77.00  60.00  166
  4  ω    -33.00  84.00   0.50    0.50    --   41.60 -82.00  30.00  234
  5  ω      8.00  34.00   0.50    0.50    --   41.60 -82.00-120.00   52
  6  ω    -29.00  35.00   0.50    0.50    --   41.60 -82.00-180.00  128
  7  ω    -30.00  69.00   0.50    0.50    --   41.60 -82.00 -90.00  198
  8  ω     98.00 192.00   0.50    0.50    --  102.30  50.00   0.00  188
  9  ω     22.00 133.00   0.50    0.50    --  102.30 -82.00 150.00  222
 10  ω     88.00 157.00   0.50    0.50    --  102.30  82.00-180.00  138
 11  ω     61.00 103.00   0.50    0.50    --  102.30 -82.00  60.00   84
 12  ω     13.00  62.00   0.50    0.50    --  102.30 -25.00-180.00   98
 13  ω    137.00 180.00   0.50    0.50    --  102.30 -25.00-180.00   86
 14  ω    106.00 156.00   0.50    0.50    --  102.30  50.00  30.00  100
 15  ω     76.00 192.00   0.50    0.50    --  102.30  38.00  90.00  232
 16  ω     30.00 143.00   0.50    0.50    --  102.30 -82.00   0.00  226
 17  ω     94.00 127.00   0.50    0.50    --  102.30 -64.00  30.00   66
 18  ω     13.00 140.00   0.50    0.50    --  102.30 -82.00 -90.00  254
 19  ω     78.00 144.00   0.50    0.50    --  102.30 -82.00-150.00  132
 20  ω     72.00  99.00   0.50    0.50    --  102.30 -82.00 -30.00   54
 21  ω     17.00  89.00   0.50    0.50    --  102.30 -64.00  30.00  144
 22  ω     13.00  66.00   0.50    0.50    --  102.30 -64.00 -90.00  106
 23  ω     77.00 102.00   0.50    0.50    --  102.30 -82.00  90.00   50
 24  ω     86.00 112.00   0.50    0.50    --  102.30 -82.00-180.00   52
 25  ω     13.00 104.00   0.50    0.50    --  102.30 -64.00 150.00  182
 26  ω     64.00 187.00   0.50    0.50    --  102.30  38.00 120.00  246
 27  ω     30.00  74.00   0.50    0.50    --   42.30 -82.00 150.00   88
 28  ω     45.00  71.00   0.50    0.50    --   42.30  38.00   0.00   52
 29  ω    152.00 178.00   0.50    0.50    --  101.60  77.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0280814000
_diffrn_orient_matrix_UB_12      0.0053253000
_diffrn_orient_matrix_UB_13      -0.0650196000
_diffrn_orient_matrix_UB_21      -0.0079421000
_diffrn_orient_matrix_UB_22      0.1308524000
_diffrn_orient_matrix_UB_23      -0.0035550000
_diffrn_orient_matrix_UB_31      0.1590318000
_diffrn_orient_matrix_UB_32      0.0074497000
_diffrn_orient_matrix_UB_33      -0.0164357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7487
_reflns_number_total             9712
_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       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         9712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0920
_refine_ls_restrained_S_all      1.087
_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)+(0.1082P)²+6.8352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2696
_refine_ls_wR_factor_ref         0.2797
_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:
 C1(H1A,H1B), C5(H5A,H5B), C40(H40A,H40B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C46(H46), C47(H47), C49(H49), C50(H50), C52(H52),
 C53(H53), C54(H54), C55(H55), C56(H56), C58(H58), C59(H59), C61(H61), C62(H62),
  C64(H64), C65(H65), C66(H66), C67(H67), C68(H68)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C71(H71A,H71B,H71C), C75(H75A,H75B,
 H75C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5489(3) 0.7667(2) 0.52100(14) 0.0442(7) Uani 1 1 d . . . . .
O2 O 0.3564(3) 0.8778(3) 0.51871(14) 0.0463(8) Uani 1 1 d . . . . .
O3 O 0.2485(3) 0.9120(2) 0.63039(14) 0.0411(7) Uani 1 1 d . . . . .
O4 O 0.2623(3) 1.0953(3) 0.59277(15) 0.0471(8) Uani 1 1 d . . . . .
N1 N 0.7541(3) 0.9549(3) 0.62795(16) 0.0372(8) Uani 1 1 d . . . . .
N2 N 0.5410(3) 1.0665(3) 0.64022(16) 0.0340(8) Uani 1 1 d . . . . .
C1 C 0.7015(4) 0.9067(4) 0.5778(2) 0.0401(10) Uani 1 1 d . . . . .
H1A H 0.727108 0.826869 0.579246 0.048 Uiso 1 1 calc R U . . .
H1B H 0.745286 0.945636 0.542113 0.048 Uiso 1 1 calc R U . . .
C2 C 0.5436(4) 0.9180(3) 0.57708(19) 0.0347(9) Uani 1 1 d . . . . .
C3 C 0.4735(4) 0.9921(3) 0.60972(18) 0.0329(9) Uani 1 1 d . . . . .
C4 C 0.3163(4) 1.0068(3) 0.60912(19) 0.0359(9) Uani 1 1 d . . . . .
C5 C 0.6962(4) 1.0690(3) 0.6301(2) 0.0376(9) Uani 1 1 d . . . . .
H5A H 0.721927 1.114841 0.593609 0.045 Uiso 1 1 calc R U . . .
H5B H 0.736198 1.104367 0.661148 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7481(4) 0.8816(4) 0.68091(19) 0.0365(9) Uani 1 1 d . . . . .
C7 C 0.7965(5) 0.7698(4) 0.6807(2) 0.0412(10) Uani 1 1 d . . . . .
H7 H 0.830943 0.744538 0.645724 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7947(5) 0.6958(4) 0.7311(2) 0.0450(11) Uani 1 1 d . . . . .
H8 H 0.828249 0.622050 0.729338 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7436(4) 0.7295(4) 0.7845(2) 0.0406(10) Uani 1 1 d . . . . .
C10 C 0.6990(5) 0.8416(4) 0.7852(2) 0.0414(10) Uani 1 1 d . . . . .
H10 H 0.666396 0.867186 0.820372 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7021(4) 0.9163(4) 0.7347(2) 0.0403(10) Uani 1 1 d . . . . .
H11 H 0.672784 0.991091 0.736789 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7308(5) 0.6455(4) 0.8376(2) 0.0418(10) Uani 1 1 d . . . . .
C13 C 0.6190(5) 0.6536(4) 0.8797(2) 0.0498(11) Uani 1 1 d . . . . .
H13 H 0.555734 0.713532 0.875127 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6016(5) 0.5739(4) 0.9278(2) 0.0538(12) Uani 1 1 d . . . . .
H14 H 0.526592 0.580338 0.955168 0.065 Uiso 1 1 calc R U . . .
C15 C 0.6954(5) 0.4845(4) 0.9355(2) 0.0533(12) Uani 1 1 d . . . . .
H15 H 0.683749 0.430570 0.967789 0.064 Uiso 1 1 calc R U . . .
C16 C 0.8061(5) 0.4763(4) 0.8947(2) 0.0534(12) Uani 1 1 d . . . . .
H16 H 0.869872 0.416783 0.899780 0.064 Uiso 1 1 calc R U . . .
C17 C 0.8234(5) 0.5560(4) 0.8462(2) 0.0481(11) Uani 1 1 d . . . . .
H17 H 0.898567 0.549020 0.818970 0.058 Uiso 1 1 calc R U . . .
C18 C 0.4704(4) 0.8554(4) 0.53700(19) 0.0380(9) Uani 1 1 d . . . . .
C19 C 0.4945(5) 0.7035(4) 0.4779(2) 0.0479(11) Uani 1 1 d . . . . .
H19A H 0.502345 0.748303 0.440673 0.072 Uiso 1 1 calc R U . . .
H19B H 0.397666 0.685409 0.488535 0.072 Uiso 1 1 calc R U . . .
H19C H 0.547169 0.634321 0.475619 0.072 Uiso 1 1 calc R U . . .
C20 C 0.0996(5) 0.9116(4) 0.6243(3) 0.0547(13) Uani 1 1 d . . . . .
H20A H 0.082072 0.927780 0.583865 0.082 Uiso 1 1 calc R U . . .
H20B H 0.055540 0.968539 0.646042 0.082 Uiso 1 1 calc R U . . .
H20C H 0.061952 0.838084 0.638829 0.082 Uiso 1 1 calc R U . . .
C21 C 0.4773(4) 1.1130(3) 0.68983(19) 0.0350(9) Uani 1 1 d . . . . .
C22 C 0.5172(4) 1.2194(3) 0.7027(2) 0.0379(9) Uani 1 1 d . . . . .
H22 H 0.581590 1.262022 0.677461 0.046 Uiso 1 1 calc R U . . .
C23 C 0.4626(4) 1.2628(4) 0.7525(2) 0.0394(10) Uani 1 1 d . . . . .
H23 H 0.490785 1.334564 0.760202 0.047 Uiso 1 1 calc R U . . .
C24 C 0.3658(4) 1.2016(3) 0.79178(19) 0.0367(9) Uani 1 1 d . . . . .
C25 C 0.3256(4) 1.0949(4) 0.7777(2) 0.0390(9) Uani 1 1 d . . . . .
H25 H 0.259795 1.052683 0.802497 0.047 Uiso 1 1 calc R U . . .
C26 C 0.3805(4) 1.0504(4) 0.72819(19) 0.0378(9) Uani 1 1 d . . . . .
H26 H 0.352986 0.978530 0.720376 0.045 Uiso 1 1 calc R U . . .
C27 C 0.3090(4) 1.2446(4) 0.8467(2) 0.0394(10) Uani 1 1 d . . . . .
C28 C 0.1748(5) 1.2133(4) 0.8708(2) 0.0441(10) Uani 1 1 d . . . . .
H28 H 0.119829 1.166968 0.851437 0.053 Uiso 1 1 calc R U . . .
C29 C 0.1222(5) 1.2501(4) 0.9227(2) 0.0494(11) Uani 1 1 d . . . . .
H29 H 0.032964 1.227711 0.938137 0.059 Uiso 1 1 calc R U . . .
C30 C 0.2012(5) 1.3199(4) 0.9520(2) 0.0520(12) Uani 1 1 d . . . . .
H30 H 0.166266 1.344331 0.987106 0.062 Uiso 1 1 calc R U . . .
C31 C 0.3328(5) 1.3528(4) 0.9281(2) 0.0542(12) Uani 1 1 d . . . . .
H31 H 0.386312 1.400851 0.947102 0.065 Uiso 1 1 calc R U . . .
C32 C 0.3863(5) 1.3154(4) 0.8766(2) 0.0472(11) Uani 1 1 d . . . . .
H32 H 0.475806 1.338074 0.861606 0.057 Uiso 1 1 calc R U . . .
O70 O 1.0441(3) 0.7087(3) 0.52395(14) 0.0450(7) Uani 1 1 d . . . . .
O72 O 0.8532(3) 0.5987(3) 0.52316(15) 0.0475(8) Uani 1 1 d . . . . .
O74 O 0.7441(3) 0.5266(2) 0.63688(14) 0.0407(7) Uani 1 1 d . . . . .
O76 O 0.7579(3) 0.3570(2) 0.60043(15) 0.0451(8) Uani 1 1 d . . . . .
N39 N 1.0377(3) 0.3665(3) 0.64866(16) 0.0365(8) Uani 1 1 d . . . . .
N41 N 1.2459(3) 0.4839(3) 0.63700(16) 0.0388(8) Uani 1 1 d . . . . .
C40 C 1.1921(4) 0.3691(3) 0.6390(2) 0.0380(9) Uani 1 1 d . . . . .
H40A H 1.232906 0.321206 0.670113 0.046 Uiso 1 1 calc R U . . .
H40B H 1.219473 0.338590 0.602505 0.046 Uiso 1 1 calc R U . . .
C42 C 1.1969(4) 0.5507(4) 0.5857(2) 0.0403(10) Uani 1 1 d . . . . .
H42A H 1.243458 0.524867 0.550804 0.048 Uiso 1 1 calc R U . . .
H42B H 1.220629 0.630176 0.586523 0.048 Uiso 1 1 calc R U . . .
C43 C 1.0389(4) 0.5388(3) 0.58382(19) 0.0351(9) Uani 1 1 d . . . . .
C44 C 0.9683(4) 0.4533(3) 0.61684(19) 0.0332(9) Uani 1 1 d . . . . .
C45 C 0.9742(4) 0.2952(3) 0.69654(19) 0.0354(9) Uani 1 1 d . . . . .
C46 C 1.0146(4) 0.1815(3) 0.7051(2) 0.0391(10) Uani 1 1 d . . . . .
H46 H 1.078559 0.152052 0.678377 0.047 Uiso 1 1 calc R U . . .
C47 C 0.9603(4) 0.1125(4) 0.7530(2) 0.0399(10) Uani 1 1 d . . . . .
H47 H 0.987948 0.036633 0.757674 0.048 Uiso 1 1 calc R U . . .
C48 C 0.8652(4) 0.1524(4) 0.7947(2) 0.0375(9) Uani 1 1 d . . . . .
C49 C 0.8243(4) 0.2671(4) 0.7847(2) 0.0388(9) Uani 1 1 d . . . . .
H49 H 0.759501 0.296438 0.811094 0.047 Uiso 1 1 calc R U . . .
C50 C 0.8775(4) 0.3368(4) 0.7371(2) 0.0393(10) Uani 1 1 d . . . . .
H50 H 0.848760 0.412371 0.731908 0.047 Uiso 1 1 calc R U . . .
C51 C 0.8114(4) 0.0798(4) 0.8473(2) 0.0404(10) Uani 1 1 d . . . . .
C52 C 0.6766(5) 0.0958(4) 0.8735(2) 0.0448(11) Uani 1 1 d . . . . .
H52 H 0.619870 0.153068 0.857067 0.054 Uiso 1 1 calc R U . . .
C53 C 0.6264(5) 0.0289(4) 0.9227(2) 0.0535(12) Uani 1 1 d . . . . .
H53 H 0.536886 0.042053 0.939186 0.064 Uiso 1 1 calc R U . . .
C54 C 0.7077(6) -0.0579(5) 0.9480(2) 0.0579(13) Uani 1 1 d . . . . .
H54 H 0.673487 -0.103327 0.981263 0.069 Uiso 1 1 calc R U . . .
C55 C 0.8414(5) -0.0758(4) 0.9228(2) 0.0543(13) Uani 1 1 d . . . . .
H55 H 0.897019 -0.133912 0.939185 0.065 Uiso 1 1 calc R U . . .
C56 C 0.8921(5) -0.0082(4) 0.8738(2) 0.0493(11) Uani 1 1 d . . . . .
H56 H 0.982070 -0.021255 0.857733 0.059 Uiso 1 1 calc R U . . .
C57 C 1.2301(4) 0.6420(4) 0.7952(2) 0.0426(10) Uani 1 1 d . . . . .
C58 C 1.2620(6) 0.7009(4) 0.7408(2) 0.0546(12) Uani 1 1 d . . . . .
H58 H 1.281085 0.778350 0.738749 0.066 Uiso 1 1 calc R U . . .
C59 C 1.2670(5) 0.6508(4) 0.6898(2) 0.0478(11) Uani 1 1 d . . . . .
H59 H 1.291712 0.694121 0.654688 0.057 Uiso 1 1 calc R U . . .
C60 C 1.2352(4) 0.5351(3) 0.6901(2) 0.0375(9) Uani 1 1 d . . . . .
C61 C 1.2034(4) 0.4753(4) 0.7442(2) 0.0411(10) Uani 1 1 d . . . . .
H61 H 1.183218 0.398052 0.746219 0.049 Uiso 1 1 calc R U . . .
C62 C 1.2006(4) 0.5264(4) 0.7952(2) 0.0419(10) Uani 1 1 d . . . . .
H62 H 1.178436 0.482650 0.830445 0.050 Uiso 1 1 calc R U . . .
C63 C 1.2233(5) 0.6987(4) 0.8500(2) 0.0438(10) Uani 1 1 d . . . . .
C64 C 1.1497(5) 0.6516(4) 0.9007(2) 0.0519(12) Uani 1 1 d . . . . .
H64 H 1.101771 0.583512 0.900258 0.062 Uiso 1 1 calc R U . . .
C65 C 1.1457(6) 0.7029(5) 0.9516(2) 0.0581(13) Uani 1 1 d . . . . .
H65 H 1.097473 0.668281 0.985107 0.070 Uiso 1 1 calc R U . . .
C66 C 1.2129(6) 0.8057(5) 0.9531(3) 0.0609(14) Uani 1 1 d . . . . .
H66 H 1.209809 0.841074 0.987218 0.073 Uiso 1 1 calc R U . . .
C67 C 1.2840(6) 0.8543(5) 0.9035(3) 0.0622(14) Uani 1 1 d . . . . .
H67 H 1.328682 0.923887 0.903926 0.075 Uiso 1 1 calc R U . . .
C68 C 1.2911(5) 0.8021(4) 0.8524(2) 0.0533(12) Uani 1 1 d . . . . .
H68 H 1.341571 0.836352 0.819433 0.064 Uiso 1 1 calc R U . . .
C69 C 0.9658(4) 0.6155(3) 0.54135(19) 0.0375(9) Uani 1 1 d . . . . .
C71 C 0.9898(5) 0.7880(4) 0.4787(2) 0.0487(11) Uani 1 1 d . . . . .
H71A H 1.006260 0.758554 0.441665 0.073 Uiso 1 1 calc R U . . .
H71B H 1.036306 0.860018 0.477551 0.073 Uiso 1 1 calc R U . . .
H71C H 0.890748 0.797898 0.486834 0.073 Uiso 1 1 calc R U . . .
C73 C 0.8123(4) 0.4386(4) 0.61628(19) 0.0374(9) Uani 1 1 d . . . . .
C75 C 0.5948(4) 0.5312(4) 0.6312(2) 0.0518(12) Uani 1 1 d . . . . .
H75A H 0.576671 0.536247 0.590746 0.078 Uiso 1 1 calc R U . . .
H75B H 0.556547 0.596848 0.647868 0.078 Uiso 1 1 calc R U . . .
H75C H 0.551794 0.463643 0.651360 0.078 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 C18 1.352(5) . ?
O1 C19 1.435(5) . ?
O2 C18 1.213(5) . ?
O3 C4 1.329(5) . ?
O3 C20 1.439(5) . ?
O4 C4 1.199(5) . ?
N1 C1 1.466(6) . ?
N1 C5 1.458(5) . ?
N1 C6 1.420(6) . ?
N2 C3 1.374(5) . ?
N2 C5 1.484(5) . ?
N2 C21 1.421(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(6) . ?
C2 C3 1.358(6) . ?
C2 C18 1.462(6) . ?
C3 C4 1.511(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.396(6) . ?
C6 C11 1.392(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(7) . ?
C9 C10 1.389(6) . ?
C9 C12 1.493(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.403(7) . ?
C12 C17 1.380(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(7) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.384(6) . ?
C21 C26 1.394(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.398(6) . ?
C24 C25 1.397(6) . ?
C24 C27 1.484(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.397(6) . ?
C27 C32 1.389(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.381(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.381(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.377(7) . ?
C32 H32 0.9300 . ?
O70 C69 1.345(5) . ?
O70 C71 1.451(5) . ?
O72 C69 1.208(5) . ?
O74 C73 1.335(5) . ?
O74 C75 1.441(5) . ?
O76 C73 1.201(5) . ?
N39 C40 1.476(5) . ?
N39 C44 1.389(5) . ?
N39 C45 1.421(5) . ?
N41 C40 1.449(5) . ?
N41 C42 1.457(6) . ?
N41 C60 1.423(6) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.520(5) . ?
C43 C44 1.354(6) . ?
C43 C69 1.473(6) . ?
C44 C73 1.502(5) . ?
C45 C46 1.393(6) . ?
C45 C50 1.395(6) . ?
C46 H46 0.9300 . ?
C46 C47 1.375(6) . ?
C47 H47 0.9300 . ?
C47 C48 1.394(6) . ?
C48 C49 1.406(6) . ?
C48 C51 1.477(6) . ?
C49 H49 0.9300 . ?
C49 C50 1.371(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.403(6) . ?
C51 C56 1.403(6) . ?
C52 H52 0.9300 . ?
C52 C53 1.374(7) . ?
C53 H53 0.9300 . ?
C53 C54 1.387(7) . ?
C54 H54 0.9300 . ?
C54 C55 1.390(7) . ?
C55 H55 0.9300 . ?
C55 C56 1.376(7) . ?
C56 H56 0.9300 . ?
C57 C58 1.388(7) . ?
C57 C62 1.397(6) . ?
C57 C63 1.492(7) . ?
C58 H58 0.9300 . ?
C58 C59 1.371(7) . ?
C59 H59 0.9300 . ?
C59 C60 1.402(6) . ?
C60 C61 1.384(6) . ?
C61 H61 0.9300 . ?
C61 C62 1.378(7) . ?
C62 H62 0.9300 . ?
C63 C64 1.389(7) . ?
C63 C68 1.394(7) . ?
C64 H64 0.9300 . ?
C64 C65 1.379(7) . ?
C65 H65 0.9300 . ?
C65 C66 1.383(8) . ?
C66 H66 0.9300 . ?
C66 C67 1.365(8) . ?
C67 H67 0.9300 . ?
C67 C68 1.386(8) . ?
C68 H68 0.9300 . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 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
C18 O1 C19 116.5(3) . . ?
C4 O3 C20 116.2(3) . . ?
C5 N1 C1 108.4(3) . . ?
C6 N1 C1 115.7(3) . . ?
C6 N1 C5 117.3(4) . . ?
C3 N2 C5 115.2(3) . . ?
C3 N2 C21 123.2(3) . . ?
C21 N2 C5 119.2(3) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.5(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 C18 120.9(4) . . ?
C18 C2 C1 118.8(4) . . ?
N2 C3 C4 115.6(3) . . ?
C2 C3 N2 122.7(4) . . ?
C2 C3 C4 121.4(4) . . ?
O3 C4 C3 111.7(3) . . ?
O4 C4 O3 125.5(4) . . ?
O4 C4 C3 122.8(4) . . ?
N1 C5 N2 111.6(3) . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
N2 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 N1 119.5(4) . . ?
C11 C6 N1 123.6(4) . . ?
C11 C6 C7 116.8(4) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C12 120.5(4) . . ?
C10 C9 C8 117.2(4) . . ?
C10 C9 C12 122.3(4) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.3(4) . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C9 120.0(4) . . ?
C17 C12 C9 122.1(4) . . ?
C17 C12 C13 117.9(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(5) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 121.0(5) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
O1 C18 C2 110.6(4) . . ?
O2 C18 O1 122.6(4) . . ?
O2 C18 C2 126.7(4) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N2 120.0(4) . . ?
C22 C21 C26 118.8(4) . . ?
C26 C21 N2 121.1(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.6(4) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C27 122.7(4) . . ?
C25 C24 C23 116.8(4) . . ?
C25 C24 C27 120.4(4) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 121.9(4) . . ?
C26 C25 H25 119.0 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.1(4) . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C24 120.6(4) . . ?
C32 C27 C24 122.0(4) . . ?
C32 C27 C28 117.4(4) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.2(4) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.5(5) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.8(5) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.0(5) . . ?
C32 C31 H31 119.5 . . ?
C27 C32 H32 119.4 . . ?
C31 C32 C27 121.2(5) . . ?
C31 C32 H32 119.4 . . ?
C69 O70 C71 116.2(4) . . ?
C73 O74 C75 116.5(3) . . ?
C44 N39 C40 114.9(3) . . ?
C44 N39 C45 124.3(3) . . ?
C45 N39 C40 119.4(3) . . ?
C40 N41 C42 108.3(3) . . ?
C60 N41 C40 116.8(4) . . ?
C60 N41 C42 117.0(3) . . ?
N39 C40 H40A 109.4 . . ?
N39 C40 H40B 109.4 . . ?
N41 C40 N39 111.4(3) . . ?
N41 C40 H40A 109.4 . . ?
N41 C40 H40B 109.4 . . ?
H40A C40 H40B 108.0 . . ?
N41 C42 H42A 109.5 . . ?
N41 C42 H42B 109.5 . . ?
N41 C42 C43 110.6(3) . . ?
H42A C42 H42B 108.1 . . ?
C43 C42 H42A 109.5 . . ?
C43 C42 H42B 109.5 . . ?
C44 C43 C42 120.8(4) . . ?
C44 C43 C69 120.2(4) . . ?
C69 C43 C42 118.7(4) . . ?
N39 C44 C73 115.5(3) . . ?
C43 C44 N39 121.7(4) . . ?
C43 C44 C73 122.5(4) . . ?
C46 C45 N39 119.3(4) . . ?
C46 C45 C50 118.6(4) . . ?
C50 C45 N39 122.0(4) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 C45 120.2(4) . . ?
C47 C46 H46 119.9 . . ?
C46 C47 H47 118.8 . . ?
C46 C47 C48 122.3(4) . . ?
C48 C47 H47 118.8 . . ?
C47 C48 C49 116.5(4) . . ?
C47 C48 C51 122.4(4) . . ?
C49 C48 C51 121.1(4) . . ?
C48 C49 H49 119.1 . . ?
C50 C49 C48 121.8(4) . . ?
C50 C49 H49 119.1 . . ?
C45 C50 H50 119.7 . . ?
C49 C50 C45 120.5(4) . . ?
C49 C50 H50 119.7 . . ?
C52 C51 C48 121.5(4) . . ?
C52 C51 C56 116.7(4) . . ?
C56 C51 C48 121.8(4) . . ?
C51 C52 H52 119.1 . . ?
C53 C52 C51 121.7(4) . . ?
C53 C52 H52 119.1 . . ?
C52 C53 H53 119.7 . . ?
C52 C53 C54 120.7(5) . . ?
C54 C53 H53 119.7 . . ?
C53 C54 H54 120.6 . . ?
C53 C54 C55 118.7(5) . . ?
C55 C54 H54 120.6 . . ?
C54 C55 H55 119.7 . . ?
C56 C55 C54 120.6(5) . . ?
C56 C55 H55 119.7 . . ?
C51 C56 H56 119.2 . . ?
C55 C56 C51 121.6(5) . . ?
C55 C56 H56 119.2 . . ?
C58 C57 C62 115.4(4) . . ?
C58 C57 C63 122.4(4) . . ?
C62 C57 C63 122.1(4) . . ?
C57 C58 H58 118.3 . . ?
C59 C58 C57 123.4(5) . . ?
C59 C58 H58 118.3 . . ?
C58 C59 H59 119.6 . . ?
C58 C59 C60 120.8(5) . . ?
C60 C59 H59 119.6 . . ?
C59 C60 N41 119.8(4) . . ?
C61 C60 N41 123.7(4) . . ?
C61 C60 C59 116.3(4) . . ?
C60 C61 H61 118.8 . . ?
C62 C61 C60 122.3(4) . . ?
C62 C61 H61 118.8 . . ?
C57 C62 H62 119.1 . . ?
C61 C62 C57 121.8(4) . . ?
C61 C62 H62 119.1 . . ?
C64 C63 C57 121.9(4) . . ?
C64 C63 C68 117.0(5) . . ?
C68 C63 C57 121.1(5) . . ?
C63 C64 H64 119.1 . . ?
C65 C64 C63 121.9(5) . . ?
C65 C64 H64 119.1 . . ?
C64 C65 H65 119.9 . . ?
C64 C65 C66 120.3(5) . . ?
C66 C65 H65 119.9 . . ?
C65 C66 H66 120.6 . . ?
C67 C66 C65 118.7(5) . . ?
C67 C66 H66 120.6 . . ?
C66 C67 H67 119.3 . . ?
C66 C67 C68 121.3(5) . . ?
C68 C67 H67 119.3 . . ?
C63 C68 H68 119.6 . . ?
C67 C68 C63 120.8(5) . . ?
C67 C68 H68 119.6 . . ?
O70 C69 C43 110.2(4) . . ?
O72 C69 O70 123.5(4) . . ?
O72 C69 C43 126.3(4) . . ?
O70 C71 H71A 109.5 . . ?
O70 C71 H71B 109.5 . . ?
O70 C71 H71C 109.5 . . ?
H71A C71 H71B 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
O74 C73 C44 110.8(3) . . ?
O76 C73 O74 125.3(4) . . ?
O76 C73 C44 123.9(4) . . ?
O74 C75 H75A 109.5 . . ?
O74 C75 H75B 109.5 . . ?
O74 C75 H75C 109.5 . . ?
H75A C75 H75B 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 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 C2 C3 17.0(6) . . . . ?
N1 C1 C2 C18 -168.2(4) . . . . ?
N1 C6 C7 C8 179.1(4) . . . . ?
N1 C6 C11 C10 -179.6(4) . . . . ?
N2 C3 C4 O3 -122.4(4) . . . . ?
N2 C3 C4 O4 55.6(6) . . . . ?
N2 C21 C22 C23 -176.1(4) . . . . ?
N2 C21 C26 C25 176.6(4) . . . . ?
C1 N1 C5 N2 63.7(4) . . . . ?
C1 N1 C6 C7 47.3(5) . . . . ?
C1 N1 C6 C11 -135.9(4) . . . . ?
C1 C2 C3 N2 6.0(6) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C1 C2 C18 O1 21.4(5) . . . . ?
C1 C2 C18 O2 -157.5(4) . . . . ?
C2 C3 C4 O3 64.2(5) . . . . ?
C2 C3 C4 O4 -117.9(5) . . . . ?
C3 N2 C5 N1 -41.6(5) . . . . ?
C3 N2 C21 C22 -150.7(4) . . . . ?
C3 N2 C21 C26 33.2(6) . . . . ?
C3 C2 C18 O1 -163.9(4) . . . . ?
C3 C2 C18 O2 17.3(7) . . . . ?
C5 N1 C1 C2 -50.2(4) . . . . ?
C5 N1 C6 C7 177.2(4) . . . . ?
C5 N1 C6 C11 -5.9(6) . . . . ?
C5 N2 C3 C2 6.2(6) . . . . ?
C5 N2 C3 C4 -167.1(3) . . . . ?
C5 N2 C21 C22 47.8(5) . . . . ?
C5 N2 C21 C26 -128.3(4) . . . . ?
C6 N1 C1 C2 83.9(4) . . . . ?
C6 N1 C5 N2 -69.6(5) . . . . ?
C6 C7 C8 C9 0.3(7) . . . . ?
C7 C6 C11 C10 -2.7(6) . . . . ?
C7 C8 C9 C10 -2.1(7) . . . . ?
C7 C8 C9 C12 174.6(4) . . . . ?
C8 C9 C10 C11 1.5(6) . . . . ?
C8 C9 C12 C13 -144.7(5) . . . . ?
C8 C9 C12 C17 32.9(7) . . . . ?
C9 C10 C11 C6 0.9(7) . . . . ?
C9 C12 C13 C14 177.1(4) . . . . ?
C9 C12 C17 C16 -177.3(4) . . . . ?
C10 C9 C12 C13 31.9(7) . . . . ?
C10 C9 C12 C17 -150.5(5) . . . . ?
C11 C6 C7 C8 2.1(6) . . . . ?
C12 C9 C10 C11 -175.2(4) . . . . ?
C12 C13 C14 C15 0.4(8) . . . . ?
C13 C12 C17 C16 0.3(7) . . . . ?
C13 C14 C15 C16 0.2(8) . . . . ?
C14 C15 C16 C17 -0.5(8) . . . . ?
C15 C16 C17 C12 0.3(8) . . . . ?
C17 C12 C13 C14 -0.6(7) . . . . ?
C18 C2 C3 N2 -168.6(4) . . . . ?
C18 C2 C3 C4 4.3(6) . . . . ?
C19 O1 C18 O2 3.9(6) . . . . ?
C19 O1 C18 C2 -175.0(4) . . . . ?
C20 O3 C4 O4 10.5(7) . . . . ?
C20 O3 C4 C3 -171.6(4) . . . . ?
C21 N2 C3 C2 -156.0(4) . . . . ?
C21 N2 C3 C4 30.7(5) . . . . ?
C21 N2 C5 N1 121.3(4) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C22 C21 C26 C25 0.5(6) . . . . ?
C22 C23 C24 C25 -0.8(6) . . . . ?
C22 C23 C24 C27 177.8(4) . . . . ?
C23 C24 C25 C26 1.4(6) . . . . ?
C23 C24 C27 C28 150.6(4) . . . . ?
C23 C24 C27 C32 -30.2(6) . . . . ?
C24 C25 C26 C21 -1.2(7) . . . . ?
C24 C27 C28 C29 178.1(4) . . . . ?
C24 C27 C32 C31 -178.8(4) . . . . ?
C25 C24 C27 C28 -30.7(6) . . . . ?
C25 C24 C27 C32 148.4(4) . . . . ?
C26 C21 C22 C23 0.1(6) . . . . ?
C27 C24 C25 C26 -177.4(4) . . . . ?
C27 C28 C29 C30 0.6(8) . . . . ?
C28 C27 C32 C31 0.4(7) . . . . ?
C28 C29 C30 C31 0.5(8) . . . . ?
C29 C30 C31 C32 -1.1(8) . . . . ?
C30 C31 C32 C27 0.7(8) . . . . ?
C32 C27 C28 C29 -1.0(7) . . . . ?
N39 C44 C73 O74 122.2(4) . . . . ?
N39 C44 C73 O76 -56.4(6) . . . . ?
N39 C45 C46 C47 176.4(4) . . . . ?
N39 C45 C50 C49 -176.2(4) . . . . ?
N41 C42 C43 C44 -16.6(6) . . . . ?
N41 C42 C43 C69 169.1(4) . . . . ?
N41 C60 C61 C62 176.7(4) . . . . ?
C40 N39 C44 C43 -5.8(6) . . . . ?
C40 N39 C44 C73 167.6(4) . . . . ?
C40 N39 C45 C46 -49.8(5) . . . . ?
C40 N39 C45 C50 127.0(4) . . . . ?
C40 N41 C42 C43 51.2(5) . . . . ?
C40 N41 C60 C59 -171.2(4) . . . . ?
C40 N41 C60 C61 13.3(6) . . . . ?
C42 N41 C40 N39 -65.9(5) . . . . ?
C42 N41 C60 C59 -40.4(5) . . . . ?
C42 N41 C60 C61 144.1(4) . . . . ?
C42 C43 C44 N39 -7.0(6) . . . . ?
C42 C43 C44 C73 180.0(4) . . . . ?
C42 C43 C69 O70 -20.5(5) . . . . ?
C42 C43 C69 O72 158.2(4) . . . . ?
C43 C44 C73 O74 -64.4(5) . . . . ?
C43 C44 C73 O76 117.0(5) . . . . ?
C44 N39 C40 N41 42.6(5) . . . . ?
C44 N39 C45 C46 144.8(4) . . . . ?
C44 N39 C45 C50 -38.5(6) . . . . ?
C44 C43 C69 O70 165.1(4) . . . . ?
C44 C43 C69 O72 -16.1(7) . . . . ?
C45 N39 C40 N41 -124.2(4) . . . . ?
C45 N39 C44 C43 160.3(4) . . . . ?
C45 N39 C44 C73 -26.3(6) . . . . ?
C45 C46 C47 C48 -0.6(7) . . . . ?
C46 C45 C50 C49 0.5(6) . . . . ?
C46 C47 C48 C49 1.5(6) . . . . ?
C46 C47 C48 C51 -177.4(4) . . . . ?
C47 C48 C49 C50 -1.4(6) . . . . ?
C47 C48 C51 C52 -149.3(4) . . . . ?
C47 C48 C51 C56 30.8(6) . . . . ?
C48 C49 C50 C45 0.4(7) . . . . ?
C48 C51 C52 C53 -179.6(4) . . . . ?
C48 C51 C56 C55 -179.9(5) . . . . ?
C49 C48 C51 C52 31.9(6) . . . . ?
C49 C48 C51 C56 -148.0(4) . . . . ?
C50 C45 C46 C47 -0.4(6) . . . . ?
C51 C48 C49 C50 177.5(4) . . . . ?
C51 C52 C53 C54 -0.6(8) . . . . ?
C52 C51 C56 C55 0.2(7) . . . . ?
C52 C53 C54 C55 0.2(8) . . . . ?
C53 C54 C55 C56 0.3(9) . . . . ?
C54 C55 C56 C51 -0.5(8) . . . . ?
C56 C51 C52 C53 0.3(7) . . . . ?
C57 C58 C59 C60 1.9(8) . . . . ?
C57 C63 C64 C65 178.7(5) . . . . ?
C57 C63 C68 C67 179.9(5) . . . . ?
C58 C57 C62 C61 0.0(7) . . . . ?
C58 C57 C63 C64 158.8(5) . . . . ?
C58 C57 C63 C68 -21.2(7) . . . . ?
C58 C59 C60 N41 -177.7(4) . . . . ?
C58 C59 C60 C61 -1.9(7) . . . . ?
C59 C60 C61 C62 1.0(6) . . . . ?
C60 N41 C40 N39 68.9(5) . . . . ?
C60 N41 C42 C43 -83.4(4) . . . . ?
C60 C61 C62 C57 -0.1(7) . . . . ?
C62 C57 C58 C59 -0.9(7) . . . . ?
C62 C57 C63 C64 -19.2(7) . . . . ?
C62 C57 C63 C68 160.8(4) . . . . ?
C63 C57 C58 C59 -179.0(5) . . . . ?
C63 C57 C62 C61 178.2(4) . . . . ?
C63 C64 C65 C66 1.7(8) . . . . ?
C64 C63 C68 C67 -0.1(7) . . . . ?
C64 C65 C66 C67 -0.6(8) . . . . ?
C65 C66 C67 C68 -0.8(8) . . . . ?
C66 C67 C68 C63 1.1(8) . . . . ?
C68 C63 C64 C65 -1.3(7) . . . . ?
C69 C43 C44 N39 167.2(4) . . . . ?
C69 C43 C44 C73 -5.8(6) . . . . ?
C71 O70 C69 O72 -3.3(6) . . . . ?
C71 O70 C69 C43 175.5(4) . . . . ?
C75 O74 C73 O76 -9.8(7) . . . . ?
C75 O74 C73 C44 171.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.958
_oxdiff_exptl_absorpt_empirical_full_min 0.575
