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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_6291
_database_code_depnum_ccdc_archive 'CCDC 2322078'
loop_
_audit_author_name
_audit_author_address
'Ningbo Gong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C7 H5 O3'
_chemical_formula_sum            'C29 H29 Cl F N4 O6'
_chemical_formula_weight         584.01
_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'
F F 0.0727 0.0534 '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                   9.1124(3)
_cell_length_b                   11.7634(4)
_cell_length_c                   25.2509(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.117(3)
_cell_angle_gamma                90
_cell_volume                     2704.87(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4959
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.466
_cell_measurement_theta_min      3.503
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.496
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995).  '
_exptl_absorpt_special_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       colourless
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.088
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23244
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.466
_diffrn_reflns_theta_min         3.503
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku 002+'
_diffrn_measurement_method       /w/k
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4959
_reflns_number_total             5176
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.059
_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)+(0.0709P)²+0.9424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C20(H20A,
 H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4A), C5(H5), C8(H8), C11(H11), C14(H14), C19(H19),
 C24(H24), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.29304(5) 0.93784(5) 0.43752(2) 0.05824(16) Uani 1 1 d . . . . .
F1 F 1.37636(13) 0.96456(14) 0.54891(5) 0.0760(4) Uani 1 1 d . . . . .
O1 O 0.18306(13) 0.55605(11) 0.48772(5) 0.0476(3) Uani 1 1 d . . . . .
O2 O 0.33188(13) 0.58673(11) 0.57455(4) 0.0436(3) Uani 1 1 d . . . . .
O3 O 0.01211(17) 0.40510(14) 0.79879(6) 0.0622(4) Uani 1 1 d . . . . .
N1 N 0.82976(14) 0.76675(12) 0.51926(5) 0.0386(3) Uani 1 1 d . . . . .
H1 H 0.796392 0.741596 0.548443 0.046 Uiso 1 1 calc R U . . .
N2 N 0.78678(15) 0.78173(14) 0.42843(5) 0.0430(3) Uani 1 1 d . . . . .
N3 N 0.56319(16) 0.72036(13) 0.38533(5) 0.0416(3) Uani 1 1 d . . . . .
N4 N 0.08223(14) 0.55625(11) 0.71499(5) 0.0347(3) Uani 1 1 d . . . . .
H4 H -0.019750 0.596335 0.715194 0.042 Uiso 1 1 d R U . . .
C1 C 1.05241(17) 0.84999(14) 0.48094(6) 0.0377(3) Uani 1 1 d . . . . .
H1A H 1.016057 0.838677 0.446445 0.045 Uiso 1 1 calc R U . . .
C2 C 1.18885(17) 0.89886(14) 0.49022(7) 0.0383(3) Uani 1 1 d . . . . .
C3 C 1.24357(19) 0.91624(17) 0.54101(7) 0.0470(4) Uani 1 1 d . . . . .
C4 C 1.1626(2) 0.8854(2) 0.58350(7) 0.0547(5) Uani 1 1 d . . . . .
H4A H 1.199460 0.897728 0.617863 0.066 Uiso 1 1 calc R U . . .
C5 C 1.02687(19) 0.83640(17) 0.57504(7) 0.0451(4) Uani 1 1 d . . . . .
H5 H 0.972286 0.815304 0.603849 0.054 Uiso 1 1 calc R U . . .
C6 C 0.97010(17) 0.81792(13) 0.52372(6) 0.0344(3) Uani 1 1 d . . . . .
C7 C 0.73973(17) 0.75141(13) 0.47572(6) 0.0344(3) Uani 1 1 d . . . . .
C8 C 0.69481(19) 0.76522(16) 0.38665(6) 0.0447(4) Uani 1 1 d . . . . .
H8 H 0.728890 0.788746 0.354162 0.054 Uiso 1 1 calc R U . . .
C9 C 0.51263(17) 0.68731(14) 0.43367(6) 0.0353(3) Uani 1 1 d . . . . .
C10 C 0.59645(16) 0.70265(13) 0.48095(6) 0.0327(3) Uani 1 1 d . . . . .
C11 C 0.53630(17) 0.66973(14) 0.52952(6) 0.0355(3) Uani 1 1 d . . . . .
H11 H 0.590152 0.680589 0.561123 0.043 Uiso 1 1 calc R U . . .
C12 C 0.39945(17) 0.62204(13) 0.53026(6) 0.0350(3) Uani 1 1 d . . . . .
C13 C 0.31591(17) 0.60471(14) 0.48189(6) 0.0370(3) Uani 1 1 d . . . . .
C14 C 0.37213(18) 0.63734(15) 0.43492(6) 0.0388(4) Uani 1 1 d . . . . .
H14 H 0.317415 0.626549 0.403497 0.047 Uiso 1 1 calc R U . . .
C15 C 0.40675(19) 0.61015(17) 0.62407(6) 0.0441(4) Uani 1 1 d . . . . .
H15A H 0.413760 0.691608 0.629585 0.053 Uiso 1 1 calc R U . . .
H15B H 0.505371 0.579084 0.624214 0.053 Uiso 1 1 calc R U . . .
C16 C 0.32116(19) 0.55635(16) 0.66756(7) 0.0444(4) Uani 1 1 d . . . . .
H16A H 0.376442 0.564188 0.700927 0.053 Uiso 1 1 calc R U . . .
H16B H 0.309785 0.475797 0.660281 0.053 Uiso 1 1 calc R U . . .
C17 C 0.17055(18) 0.60917(15) 0.67290(6) 0.0398(4) Uani 1 1 d . . . . .
H17A H 0.182492 0.689468 0.680663 0.048 Uiso 1 1 calc R U . . .
H17B H 0.116475 0.602685 0.639222 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1509(2) 0.56583(16) 0.76931(6) 0.0434(4) Uani 1 1 d . . . . .
H18A H 0.173283 0.644790 0.777185 0.052 Uiso 1 1 calc R U . . .
H18B H 0.241878 0.523003 0.771375 0.052 Uiso 1 1 calc R U . . .
C19 C 0.0459(2) 0.5199(2) 0.80911(7) 0.0573(5) Uani 1 1 d . . . . .
H19 H 0.008650 0.561993 0.836754 0.069 Uiso 1 1 calc R U . . .
C20 C -0.0514(2) 0.3918(2) 0.74735(9) 0.0594(5) Uani 1 1 d . . . . .
H20A H -0.143480 0.433225 0.744836 0.071 Uiso 1 1 calc R U . . .
H20B H -0.072826 0.312024 0.741149 0.071 Uiso 1 1 calc R U . . .
C21 C 0.0484(2) 0.43435(15) 0.70516(7) 0.0458(4) Uani 1 1 d . . . . .
H21A H 0.138601 0.390469 0.706025 0.055 Uiso 1 1 calc R U . . .
H21B H 0.000690 0.425364 0.670437 0.055 Uiso 1 1 calc R U . . .
C22 C 0.0921(2) 0.5421(2) 0.44047(8) 0.0539(5) Uani 1 1 d . . . . .
H22A H 0.141695 0.494730 0.415851 0.081 Uiso 1 1 calc R U . . .
H22B H 0.072874 0.615077 0.424688 0.081 Uiso 1 1 calc R U . . .
H22C H 0.001025 0.507119 0.449297 0.081 Uiso 1 1 calc R U . . .
O4 O 0.79598(14) 0.68273(11) 0.63633(5) 0.0467(3) Uani 1 1 d . . . . .
O5 O 0.83512(13) 0.65958(11) 0.72350(5) 0.0481(3) Uani 1 1 d . . . . .
O6 O 0.39955(15) 0.85836(14) 0.80109(5) 0.0583(4) Uani 1 1 d . . . . .
H6 H 0.447989 0.821854 0.823190 0.087 Uiso 1 1 calc R U . . .
C23 C 0.64777(16) 0.78589(13) 0.69507(6) 0.0318(3) Uani 1 1 d . . . . .
C24 C 0.57940(17) 0.78177(14) 0.74327(6) 0.0356(3) Uani 1 1 d . . . . .
H24 H 0.606568 0.726392 0.768023 0.043 Uiso 1 1 calc R U . . .
C25 C 0.47030(17) 0.86010(15) 0.75482(6) 0.0391(4) Uani 1 1 d . . . . .
C26 C 0.43320(19) 0.94453(15) 0.71807(7) 0.0430(4) Uani 1 1 d . . . . .
H26 H 0.363049 0.998791 0.725930 0.052 Uiso 1 1 calc R U . . .
C27 C 0.50043(19) 0.94781(14) 0.66995(7) 0.0414(4) Uani 1 1 d . . . . .
H27 H 0.474477 1.003938 0.645410 0.050 Uiso 1 1 calc R U . . .
C28 C 0.60626(17) 0.86815(14) 0.65793(6) 0.0368(3) Uani 1 1 d . . . . .
H28 H 0.649349 0.869729 0.625120 0.044 Uiso 1 1 calc R U . . .
C29 C 0.76820(17) 0.70323(13) 0.68303(6) 0.0349(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7251(16) . ?
F1 C3 1.345(2) . ?
O1 C13 1.3520(19) . ?
O1 C22 1.437(2) . ?
O2 C12 1.3612(18) . ?
O2 C15 1.429(2) . ?
O3 C19 1.408(3) . ?
O3 C20 1.411(3) . ?
N1 H1 0.8600 . ?
N1 C6 1.414(2) . ?
N1 C7 1.359(2) . ?
N2 C7 1.332(2) . ?
N2 C8 1.337(2) . ?
N3 C8 1.310(2) . ?
N3 C9 1.377(2) . ?
N4 H4 1.0423 . ?
N4 C17 1.4927(19) . ?
N4 C18 1.491(2) . ?
N4 C21 1.486(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.382(2) . ?
C1 C6 1.390(2) . ?
C2 C3 1.374(2) . ?
C3 C4 1.373(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(2) . ?
C7 C10 1.437(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(2) . ?
C9 C14 1.410(2) . ?
C10 C11 1.416(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(2) . ?
C12 C13 1.430(2) . ?
C13 C14 1.364(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.509(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.517(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.513(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.512(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O4 C29 1.2389(19) . ?
O5 C29 1.278(2) . ?
O6 H6 0.8200 . ?
O6 C25 1.355(2) . ?
C23 C24 1.389(2) . ?
C23 C28 1.390(2) . ?
C23 C29 1.506(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.394(2) . ?
C25 C26 1.392(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.386(2) . ?
C28 H28 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
C13 O1 C22 116.70(13) . . ?
C12 O2 C15 116.37(12) . . ?
C19 O3 C20 110.88(15) . . ?
C6 N1 H1 115.2 . . ?
C7 N1 H1 115.2 . . ?
C7 N1 C6 129.64(13) . . ?
C7 N2 C8 117.08(14) . . ?
C8 N3 C9 115.31(14) . . ?
C17 N4 H4 108.6 . . ?
C18 N4 H4 107.8 . . ?
C18 N4 C17 113.87(13) . . ?
C21 N4 H4 105.0 . . ?
C21 N4 C17 113.42(13) . . ?
C21 N4 C18 107.71(13) . . ?
C2 C1 H1A 120.4 . . ?
C2 C1 C6 119.28(14) . . ?
C6 C1 H1A 120.4 . . ?
C1 C2 Cl1 119.81(13) . . ?
C3 C2 Cl1 119.30(13) . . ?
C3 C2 C1 120.89(15) . . ?
F1 C3 C2 119.65(16) . . ?
F1 C3 C4 120.13(16) . . ?
C4 C3 C2 120.21(16) . . ?
C3 C4 H4A 120.1 . . ?
C3 C4 C5 119.72(16) . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.72(16) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 N1 124.47(14) . . ?
C1 C6 C5 119.19(14) . . ?
C5 C6 N1 116.34(14) . . ?
N1 C7 C10 120.13(13) . . ?
N2 C7 N1 119.00(14) . . ?
N2 C7 C10 120.87(14) . . ?
N2 C8 H8 115.6 . . ?
N3 C8 N2 128.71(15) . . ?
N3 C8 H8 115.6 . . ?
N3 C9 C10 121.87(14) . . ?
N3 C9 C14 118.12(14) . . ?
C10 C9 C14 120.01(14) . . ?
C9 C10 C7 116.13(13) . . ?
C9 C10 C11 119.03(14) . . ?
C11 C10 C7 124.83(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.42(14) . . ?
C12 C11 H11 119.8 . . ?
O2 C12 C11 125.21(14) . . ?
O2 C12 C13 114.55(13) . . ?
C11 C12 C13 120.23(14) . . ?
O1 C13 C12 114.70(14) . . ?
O1 C13 C14 125.47(15) . . ?
C14 C13 C12 119.83(14) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.47(14) . . ?
C13 C14 H14 119.8 . . ?
O2 C15 H15A 110.1 . . ?
O2 C15 H15B 110.1 . . ?
O2 C15 C16 108.23(14) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 112.73(14) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
N4 C17 C16 113.94(13) . . ?
N4 C17 H17A 108.8 . . ?
N4 C17 H17B 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
N4 C18 H18A 109.8 . . ?
N4 C18 H18B 109.8 . . ?
N4 C18 C19 109.28(15) . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
O3 C19 C18 111.04(16) . . ?
O3 C19 H19 124.5 . . ?
C18 C19 H19 124.5 . . ?
O3 C20 H20A 109.2 . . ?
O3 C20 H20B 109.2 . . ?
O3 C20 C21 112.01(16) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
N4 C21 C20 109.16(16) . . ?
N4 C21 H21A 109.8 . . ?
N4 C21 H21B 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 O6 H6 109.5 . . ?
C24 C23 C28 119.73(14) . . ?
C24 C23 C29 120.56(13) . . ?
C28 C23 C29 119.71(14) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.46(14) . . ?
C25 C24 H24 119.8 . . ?
O6 C25 C24 122.41(15) . . ?
O6 C25 C26 118.29(15) . . ?
C26 C25 C24 119.30(15) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.11(15) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.55(15) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.80(15) . . ?
C27 C28 H28 120.1 . . ?
O4 C29 O5 125.06(15) . . ?
O4 C29 C23 119.60(14) . . ?
O5 C29 C23 115.34(13) . . ?

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 C2 C3 F1 0.8(3) . . . . ?
Cl1 C2 C3 C4 -179.77(17) . . . . ?
F1 C3 C4 C5 179.8(2) . . . . ?
O1 C13 C14 C9 -179.93(16) . . . . ?
O2 C12 C13 O1 0.0(2) . . . . ?
O2 C12 C13 C14 179.66(15) . . . . ?
O2 C15 C16 C17 -65.1(2) . . . . ?
O3 C20 C21 N4 -58.4(2) . . . . ?
N1 C7 C10 C9 -178.41(14) . . . . ?
N1 C7 C10 C11 1.4(2) . . . . ?
N2 C7 C10 C9 1.3(2) . . . . ?
N2 C7 C10 C11 -178.88(16) . . . . ?
N3 C9 C10 C7 -1.9(2) . . . . ?
N3 C9 C10 C11 178.21(15) . . . . ?
N3 C9 C14 C13 -178.97(16) . . . . ?
N4 C18 C19 O3 59.8(2) . . . . ?
C1 C2 C3 F1 -179.63(17) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C1 C6 N1 -179.68(15) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 N1 179.87(19) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 N1 C7 N2 4.0(3) . . . . ?
C6 N1 C7 C10 -176.31(15) . . . . ?
C6 C1 C2 Cl1 179.37(13) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 N1 C6 C1 -9.1(3) . . . . ?
C7 N1 C6 C5 170.84(17) . . . . ?
C7 N2 C8 N3 -1.6(3) . . . . ?
C7 C10 C11 C12 -178.82(15) . . . . ?
C8 N2 C7 N1 -179.99(16) . . . . ?
C8 N2 C7 C10 0.3(2) . . . . ?
C8 N3 C9 C10 0.9(2) . . . . ?
C8 N3 C9 C14 -179.39(16) . . . . ?
C9 N3 C8 N2 0.9(3) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 O2 179.52(15) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 O1 179.44(15) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 O2 C15 C16 -175.42(15) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C14 C9 C10 C7 178.40(15) . . . . ?
C14 C9 C10 C11 -1.5(2) . . . . ?
C15 O2 C12 C11 5.1(2) . . . . ?
C15 O2 C12 C13 -175.48(15) . . . . ?
C15 C16 C17 N4 178.96(14) . . . . ?
C17 N4 C18 C19 174.54(15) . . . . ?
C17 N4 C21 C20 -175.29(14) . . . . ?
C18 N4 C17 C16 61.28(19) . . . . ?
C18 N4 C21 C20 57.75(18) . . . . ?
C19 O3 C20 C21 58.4(2) . . . . ?
C20 O3 C19 C18 -58.8(2) . . . . ?
C21 N4 C17 C16 -62.38(19) . . . . ?
C21 N4 C18 C19 -58.76(18) . . . . ?
C22 O1 C13 C12 177.02(16) . . . . ?
C22 O1 C13 C14 -2.6(3) . . . . ?
O6 C25 C26 C27 -178.59(16) . . . . ?
C23 C24 C25 O6 179.21(16) . . . . ?
C23 C24 C25 C26 -1.7(2) . . . . ?
C24 C23 C28 C27 2.1(2) . . . . ?
C24 C23 C29 O4 157.27(15) . . . . ?
C24 C23 C29 O5 -23.1(2) . . . . ?
C24 C25 C26 C27 2.3(3) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C26 C27 C28 C23 -1.6(2) . . . . ?
C28 C23 C24 C25 -0.5(2) . . . . ?
C28 C23 C29 O4 -23.7(2) . . . . ?
C28 C23 C29 O5 155.93(15) . . . . ?
C29 C23 C24 C25 178.48(14) . . . . ?
C29 C23 C28 C27 -176.86(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6331
_database_code_depnum_ccdc_archive 'CCDC 2322080'
loop_
_audit_author_name
_audit_author_address
'Ningbo Gong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, 0.5(C7 H6 O3)'
_chemical_formula_sum            'C25.50 H27 Cl F N4 O4.50'
_chemical_formula_weight         515.96
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.73274(5)
_cell_length_b                   12.20698(10)
_cell_length_c                   14.35665(12)
_cell_angle_alpha                65.3898(8)
_cell_angle_beta                 84.3011(6)
_cell_angle_gamma                89.3070(6)
_cell_volume                     1225.341(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    35704
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1790
_cell_measurement_theta_min      3.4170
_shelx_estimated_absorpt_T_max   1.0
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    1.813
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.144
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     69.00  95.00   0.50    0.05    --   47.76  59.00 109.00   52
  2  ω    108.00 161.00   0.50    0.10    --  106.68  59.00 109.00  106
  3  ω    136.00 178.00   0.50    0.10    --  106.68  45.00  30.00   84
  4  ω    129.00 177.00   0.50    0.10    --  106.68  61.00   0.00   96
  5  ω    111.00 173.00   0.50    0.10    --  106.68  30.00  90.00  124
  6  ω     65.00  91.00   0.50    0.05    --   47.76  57.00-150.00   52
  7  ω     91.00 117.00   0.50    0.10    --  106.68  61.00-180.00   52
  8  ω    146.00 171.00   0.50    0.10    --  106.68  61.00-180.00   50
  9  ω     36.00 105.00   0.50    0.10    --  106.68 -77.00 -30.00  138
 10  ω     34.00  72.00   0.50    0.10    --  106.68 -59.00 -30.00   76
 11  ω     35.00  61.00   0.50    0.10    --  106.68 -61.00-150.00   52
 12  ω     -5.00  43.00   0.50    0.05    --   47.76 -59.00 -30.00   96
 13  ω    -22.00  27.00   0.50    0.05    --  -47.76  19.00  90.00   98
 14  ω    -59.00   0.00   0.50    0.05    --  -47.76  59.00 109.00  118
 15  ω     37.00  97.00   0.50    0.10    --  106.68-125.00  90.00  120
 16  ω     80.00 105.00   0.50    0.10    --  106.68 -94.00 150.00   50
 17  ω    -23.00  27.00   0.50    0.05    --  -47.76  19.00-150.00  100
 18  ω    -60.00 -28.00   0.50    0.10    -- -101.00  77.00-180.00   64
 19  ω    -96.00 -66.00   0.50    0.10    -- -101.00  77.00-180.00   60
 20  ω    -65.00 -40.00   0.50    0.10    -- -101.00  61.00 -90.00   50
 21  ω    -68.00 -28.00   0.50    0.10    -- -101.00  61.00 -60.00   80
 22  ω    -57.00 -31.00   0.50    0.10    -- -101.00  61.00 -30.00   52
 23  ω    -65.00 -40.00   0.50    0.10    -- -101.00  59.00 109.00   50
 24  ω   -171.00 -78.00   0.50    0.10    -- -101.00 -77.00 -60.00  186
 25  ω   -155.00 -81.00   0.50    0.10    -- -101.00 -77.00-120.00  148
 26  ω   -162.00-135.00   0.50    0.10    -- -101.00 -61.00-150.00   54
 27  ω   -131.00 -92.00   0.50    0.10    -- -101.00 -61.00-150.00   78
 28  ω   -156.00 -85.00   0.50    0.10    -- -101.00 -61.00-120.00  142
 29  ω   -150.00-125.00   0.50    0.10    -- -101.00 -61.00 -90.00   50
 30  ω   -110.00 -80.00   0.50    0.10    -- -101.00 -77.00 -90.00   60
 31  ω   -110.00 -85.00   0.50    0.10    -- -101.00 -61.00 -90.00   50
 32  ω   -153.00-128.00   0.50    0.10    -- -101.00 -59.00 -30.00   50
 33  ω   -173.00 -93.00   0.50    0.10    -- -101.00 -45.00   0.00  160
 34  ω   -173.00 -84.00   0.50    0.10    -- -101.00 -61.00  60.00  178
 35  ω   -122.00 -37.00   0.50    0.05    --  -47.76 -19.00 150.00  170
 36  ω    -91.00 -65.00   0.50    0.05    --  -47.76 -59.00 -30.00   52
 37  ω   -174.00-136.00   0.50    0.10    -- -101.00 -15.00-180.00   76
 38  ω   -111.00 -77.00   0.50    0.05    --  -47.76-125.00 -60.00   68
 39  ω   -116.00 -75.00   0.50    0.05    --  -47.76-125.00   0.00   82
 40  ω   -171.00-134.00   0.50    0.10    -- -101.00 -94.00 -30.00   74
 41  ω   -129.00 -94.00   0.50    0.10    -- -101.00 -94.00 -30.00   70
 42  ω   -118.00 -74.00   0.50    0.05    --  -47.76-125.00 120.00   88
 43  ω   -144.00-118.00   0.50    0.10    -- -101.00-102.00  95.00   52
 44  ω    -43.00 -17.00   0.50    0.05    --    8.00 131.00 119.43   52
 45  ω    -41.00 -16.00   0.50    0.05    --    8.00 127.00  30.61   50
 46  ω    -24.00   1.00   0.50    0.05    --   12.00 104.00-134.00   50
 47  ω    -11.00  15.00   0.50    0.05    --   16.00  98.00 -26.82   52
 48  ω    -14.00  12.00   0.50    0.05    --   20.00 102.00-100.06   52
 49  ω     -4.00  21.00   0.50    0.05    --   28.00  97.00-173.09   50
 50  ω      6.00  31.00   0.50    0.05    --   36.00  92.00-115.53   50
 51  ω     13.00  38.00   0.50    0.05    --   40.00  87.00 -81.76   50
 52  ω     15.00  40.00   0.50    0.05    --   44.00  90.00  68.51   50
 53  ω     16.00  41.00   0.50    0.05    --   44.00  88.00 -48.76   50
 54  ω    -58.00 -28.00   0.50    0.05    --  -47.76 -77.00 -90.00   60
 55  ω    -51.00 -25.00   0.50    0.05    --  -47.76 -77.00 150.00   52
 56  ω     50.00  91.00   0.50    0.05    --   47.76-125.00  30.00   82
 57  ω     32.00  58.00   0.50    0.05    --   52.00  75.00 136.84   52
 58  ω     34.00  65.00   0.50    0.05    --   56.00  76.00  24.16   62
 59  ω     33.00  59.00   0.50    0.05    --   56.00  77.00-175.16   52
 60  ω     35.00  76.00   0.50    0.05    --   56.00  76.00  64.60   82
 61  ω     97.00 123.00   0.50    0.05    --   56.00  77.00-175.16   52
 62  ω     35.00  61.00   0.50    0.05    --   56.00  76.00-132.75   52
 63  ω    -67.00 -41.00   0.50    0.05    --  -60.00 -71.00-158.45   52
 64  ω     38.00  63.00   0.50    0.05    --   60.00  75.00 146.53   50
 65  ω     39.00  73.00   0.50    0.05    --   60.00  73.00  53.21   68
 66  ω     39.00  65.00   0.50    0.05    --   60.00  72.00 -13.00   52
 67  ω    -68.00 -42.00   0.50    0.05    --  -64.00 -74.00 125.38   52
 68  ω    -70.00 -44.00   0.50    0.05    --  -64.00 -72.00-144.01   52
 69  ω    -69.00 -43.00   0.50    0.05    --  -64.00 -74.00 162.32   52
 70  ω   -134.00-108.00   0.50    0.05    --  -68.00 -69.00-178.55   52
 71  ω    -75.00 -49.00   0.50    0.05    --  -68.00 -70.00-103.24   52
 72  ω    -73.00 -48.00   0.50    0.05    --  -68.00 -70.00 -68.98   50
 73  ω    -73.00 -48.00   0.50    0.05    --  -68.00 -69.00-178.55   50
 74  ω    -75.00 -49.00   0.50    0.05    --  -68.00 -67.00 -90.02   52
 75  ω     46.00  72.00   0.50    0.05    --   68.00  75.00   1.67   52
 76  ω     45.00  71.00   0.50    0.05    --   68.00  77.00 -83.55   52
 77  ω     45.00  71.00   0.50    0.05    --   68.00  77.00  81.68   52
 78  ω    -90.00 -50.00   0.50    0.05    --  -72.00 -75.00  83.53   80
 79  ω    -79.00 -49.00   0.50    0.05    --  -72.00 -76.00  43.60   60
 80  ω    -75.00 -50.00   0.50    0.05    --  -72.00 -74.00  -0.70   50
 81  ω   -140.00-114.00   0.50    0.05    --  -72.00 -75.00  83.53   52
 82  ω    -76.00 -50.00   0.50    0.05    --  -72.00 -76.00-110.02   52
 83  ω    -75.00 -49.00   0.50    0.05    --  -72.00 -76.00 -36.49   52
 84  ω    -81.00 -55.00   0.50    0.10    --  -76.00 -73.00 123.27   52
 85  ω    -83.00 -58.00   0.50    0.10    --  -80.00 -75.00 173.84   50
 86  ω    -84.00 -58.00   0.50    0.10    --  -80.00 -74.00  18.91   52
 87  ω    -87.00 -61.00   0.50    0.10    --  -80.00 -67.00 -74.39   52
 88  ω   -155.00-129.00   0.50    0.10    --  -84.00 -70.00-146.32   52
 89  ω    -88.00 -62.00   0.50    0.10    --  -84.00 -75.00-129.88   52
 90  ω    -90.00 -64.00   0.50    0.10    --  -84.00 -70.00-146.32   52
 91  ω    -87.00 -62.00   0.50    0.10    --  -84.00 -75.00 115.38   50
 92  ω   -148.00-122.00   0.50    0.10    --  -84.00 -75.00 115.38   52
 93  ω    -88.00 -62.00   0.50    0.10    --  -84.00 -74.00-166.29   52
 94  ω    -90.00 -64.00   0.50    0.10    --  -84.00 -73.00  42.06   52
 95  ω    -88.00 -62.00   0.50    0.10    --  -84.00 -75.00 157.94   52
 96  ω    -93.00 -67.00   0.50    0.10    --  -84.00 -61.00-168.28   52
 97  ω    -89.00 -63.00   0.50    0.10    --  -84.00 -73.00 -87.93   52
 98  ω    -88.00 -62.00   0.50    0.10    --  -84.00 -74.00-106.72   52
 99  ω   -144.00-118.00   0.50    0.10    --  -88.00 -73.00   9.97   52
100  ω   -130.00-104.00   0.50    0.10    --  -88.00 -64.00 157.74   52
101  ω    -98.00 -72.00   0.50    0.10    --  -88.00 -63.00-129.32   52
102  ω   -161.00-135.00   0.50    0.10    --  -88.00 -64.00 157.74   52
103  ω    -91.00 -65.00   0.50    0.10    --  -88.00 -76.00 -41.19   52
104  ω   -140.00-114.00   0.50    0.10    --  -88.00 -76.00 -41.19   52
105  ω   -103.00 -67.00   0.50    0.10    --  -88.00 -73.00   9.97   72
106  ω   -160.00-109.00   0.50    0.10    --  -88.00 -74.00 -19.13  102
107  ω    -91.00 -65.00   0.50    0.10    --  -88.00 -76.00 -66.91   52
108  ω    -92.00 -66.00   0.50    0.10    --  -88.00 -75.00  89.61   52
109  ω    -91.00 -66.00   0.50    0.10    --  -88.00 -74.00 -19.13   50
110  ω    -97.00 -68.00   0.50    0.10    --  -88.00 -72.00  93.09   58
111  ω    -96.00 -70.00   0.50    0.10    --  -88.00 -64.00 157.74   52
112  ω    -99.00 -70.00   0.50    0.10    --  -92.00 -74.00 138.04   58
113  ω   -165.00-125.00   0.50    0.10    --  -92.00 -74.00 138.04   80
114  ω    -99.00 -69.00   0.50    0.10    --  -92.00 -76.00  41.85   60
115  ω   -163.00-105.00   0.50    0.10    --  -92.00 -76.00  41.85  116
116  ω   -169.00-143.00   0.50    0.10    --  -96.00 -77.00   3.47   52
117  ω   -139.00 -73.00   0.50    0.10    --  -96.00 -77.00   3.47  132
118  ω   -102.00 -76.00   0.50    0.10    --  -96.00 -69.00-157.78   52
119  ω   -125.00 -86.00   0.50    0.10    -- -101.00 -55.00  44.68   78
120  ω   -104.00 -79.00   0.50    0.10    -- -101.00 -79.00-110.33   50
121  ω   -170.00-134.00   0.50    0.10    -- -101.00 -79.00-110.33   72
122  ω    -53.00 -28.00   0.50    0.10    -- -101.00  77.00-150.00   50
123  ω   -100.00 -74.00   0.50    0.10    -- -101.00  77.00-150.00   52
124  ω    -53.00 -28.00   0.50    0.10    -- -101.00 141.00-150.69   50
125  ω   -123.00 -71.00   0.50    0.10    -- -101.00 141.00-150.69  104
126  ω   -132.00 -78.00   0.50    0.10    -- -101.00 -76.00 -96.52  108
127  ω    -63.00 -29.00   0.50    0.10    -- -101.00 111.00 115.99   68
128  ω   -107.00 -81.00   0.50    0.10    -- -101.00 -74.00-166.82   52
129  ω   -170.00-141.00   0.50    0.10    -- -101.00 -74.00-166.82   58
130  ω   -109.00 -81.00   0.50    0.10    -- -101.00 -69.00 157.68   56
131  ω   -111.00 -70.00   0.50    0.10    -- -101.00 125.00 -60.00   82
132  ω    -53.00 -28.00   0.50    0.10    -- -101.00  61.00 120.00   50
133  ω   -108.00 -77.00   0.50    0.10    -- -101.00 111.00 115.99   62
134  ω   -123.00 -82.00   0.50    0.10    -- -101.00 -67.00 123.02   82
135  ω   -116.00 -82.00   0.50    0.10    -- -101.00 -67.00 -28.27   68
136  ω   -173.00-148.00   0.50    0.10    -- -101.00 -67.00 -28.27   50
137  ω   -119.00 -81.00   0.50    0.10    -- -101.00 -77.00  90.00   76
138  ω     60.00 105.00   0.50    0.10    --  106.68-125.00-120.00   90
139  ω     36.00  65.00   0.50    0.10    --  106.68 -61.00 120.00   58
140  ω     84.00 110.00   0.50    0.10    --  106.68-125.00  60.00   52
141  ω     56.00  82.00   0.50    0.10    --  106.68-125.00  60.00   52
142  ω     53.00  99.00   0.50    0.10    --  106.68-102.00  95.00   92
143  ω     37.00 102.00   0.50    0.10    --  106.68 -94.00 -60.00  130
144  ω     70.00  96.00   0.50    0.10    --  106.68 -94.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4905
_reflns_number_total             4977
_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 1.171.41.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0053(3)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         4977
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.009
_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)+(0.0215P)²+1.2280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A) \\sim Ueq,
Uanis(C5A) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C5A)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Rigid body (RIGU) restrains
 C5A, C4A, C3A, C2A, C1A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5, C4, C3, C2, C1, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H1A)=Sof(Cl1A)=Sof(F1A)=Sof(C6A)=Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(C3A)=
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=1-FVAR(1)
 Sof(H1B)=Sof(Cl1)=Sof(F1)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(C2)=
 Sof(C1)=Sof(H1)=Sof(C6)=FVAR(1)
 Fixed Sof: O6(0.5) H6(0.5) O4(0.5) O5(0.5) H5B(0.5) C26(0.5) C27(0.5)
 H27(0.5) C28(0.5) H28(0.5) C23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5)
 C29(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1B), N1(H1A), C8(H8), C11(H11), C14(H14), C1A(H1AA), C4A(H4A), C5A(H5A),
 C5(H5), C4(H4), C1(H1), C27(H27), C28(H28), C24(H24), C25(H25)
5.c Fitted hexagon refined as free rotating group:
 C6A(C1A,C2A,C3A,C4A,C5A), C5(C4,C3,C2,C1,C6), C26(C27,C28,C23,C24,C25)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
5.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O5(H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.50749(15) 0.39645(10) 0.84287(8) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.68337(15) 0.25743(10) 0.77919(8) 0.0254(2) Uani 1 1 d . . . . .
O3 O 0.4108(2) -0.22442(13) 0.75442(12) 0.0487(4) Uani 1 1 d . . . . .
N1 N 0.84900(16) 0.50868(12) 0.38703(10) 0.0224(3) Uani 1 1 d . . . . .
H1B H 0.865388 0.435322 0.432914 0.027 Uiso 0.9002(16) 1 calc R U P A -1
H1A H 0.872738 0.434439 0.427998 0.027 Uiso 0.0998(16) 1 calc R U P A -2
N2 N 0.72689(17) 0.69242(12) 0.36357(10) 0.0248(3) Uani 1 1 d . . . . .
N3 N 0.55718(17) 0.71831(12) 0.50102(10) 0.0237(3) Uani 1 1 d . . . . .
N4 N 0.54682(19) -0.04335(12) 0.80749(10) 0.0279(3) Uani 1 1 d . . . . .
C7 C 0.75760(19) 0.57877(14) 0.42611(12) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.6255(2) 0.75442(15) 0.40494(13) 0.0254(3) Uani 1 1 d . . . . .
H8 H 0.600116 0.833973 0.359225 0.031 Uiso 1 1 calc R U . . .
C9 C 0.59463(19) 0.60369(14) 0.56832(12) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.69568(19) 0.52847(14) 0.53374(12) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.72779(19) 0.41043(14) 0.60466(12) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.796168 0.359280 0.581989 0.026 Uiso 1 1 calc R U . . .
C12 C 0.66136(19) 0.36906(14) 0.70571(12) 0.0215(3) Uani 1 1 d . . . . .
C13 C 0.56113(19) 0.44665(14) 0.74100(12) 0.0216(3) Uani 1 1 d . . . . .
C14 C 0.52772(19) 0.56100(14) 0.67318(12) 0.0216(3) Uani 1 1 d . . . . .
H14 H 0.459620 0.611753 0.696464 0.026 Uiso 1 1 calc R U . . .
C15 C 0.7871(2) 0.17775(14) 0.74750(13) 0.0259(3) Uani 1 1 d . . . . .
H15A H 0.905723 0.213164 0.719752 0.031 Uiso 1 1 calc R U . . .
H15B H 0.733795 0.163770 0.693322 0.031 Uiso 1 1 calc R U . . .
C16 C 0.7942(2) 0.06091(15) 0.84184(13) 0.0302(4) Uani 1 1 d . . . . .
H16A H 0.836544 0.078451 0.897218 0.036 Uiso 1 1 calc R U . . .
H16B H 0.879439 0.008739 0.825358 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6206(2) -0.00764(15) 0.88169(13) 0.0307(4) Uani 1 1 d . . . . .
H17A H 0.635497 -0.080984 0.944906 0.037 Uiso 1 1 calc R U . . .
H17B H 0.536732 0.043315 0.900839 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3778(3) -0.10412(17) 0.85309(14) 0.0352(4) Uani 1 1 d . . . . .
H18A H 0.298472 -0.048040 0.868293 0.042 Uiso 1 1 calc R U . . .
H18B H 0.391886 -0.174248 0.918792 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2990(3) -0.14631(19) 0.78079(15) 0.0408(5) Uani 1 1 d . . . . .
H19A H 0.186387 -0.189064 0.814086 0.049 Uiso 1 1 calc R U . . .
H19B H 0.276494 -0.075472 0.717310 0.049 Uiso 1 1 calc R U . . .
C20 C 0.5741(3) -0.16344(19) 0.70787(16) 0.0413(5) Uani 1 1 d . . . . .
H20A H 0.556259 -0.091525 0.644140 0.050 Uiso 1 1 calc R U . . .
H20B H 0.651644 -0.217535 0.688690 0.050 Uiso 1 1 calc R U . . .
C21 C 0.6594(3) -0.12511(16) 0.77994(14) 0.0340(4) Uani 1 1 d . . . . .
H21A H 0.680716 -0.196954 0.842970 0.041 Uiso 1 1 calc R U . . .
H21B H 0.772850 -0.083886 0.746230 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4202(2) 0.47280(15) 0.88489(13) 0.0278(4) Uani 1 1 d . . . . .
H22A H 0.314057 0.501969 0.851351 0.042 Uiso 1 1 calc R U . . .
H22B H 0.497057 0.541612 0.872925 0.042 Uiso 1 1 calc R U . . .
H22C H 0.389729 0.426920 0.959099 0.042 Uiso 1 1 calc R U . . .
Cl1A Cl 1.1583(6) 0.3756(4) 0.1352(4) 0.0391(14) Uani 0.0998(16) 1 d . . P A -2
F1A F 1.112(4) 0.617(3) -0.021(2) 0.045(6) Uani 0.0998(16) 1 d . . P A -2
C6A C 0.909(2) 0.5580(15) 0.2740(10) 0.008(3) Uani 0.0998(16) 1 d G U P A -2
C1A C 0.999(2) 0.4701(11) 0.2532(10) 0.010(3) Uani 0.0998(16) 1 d G U P A -2
H1AA H 1.015787 0.393978 0.307568 0.012 Uiso 0.0998(16) 1 calc R U P A -2
C2A C 1.0645(18) 0.4935(12) 0.1527(11) 0.011(3) Uani 0.0998(16) 1 d G U P A -2
C3A C 1.040(2) 0.6049(15) 0.0731(9) 0.028(4) Uani 0.0998(16) 1 d G U P A -2
C4A C 0.950(2) 0.6928(12) 0.0940(11) 0.033(5) Uani 0.0998(16) 1 d G U P A -2
H4A H 0.933646 0.768927 0.039594 0.040 Uiso 0.0998(16) 1 calc R U P A -2
C5A C 0.885(2) 0.6694(13) 0.1944(13) 0.009(3) Uani 0.0998(16) 1 d G U P A -2
H5A H 0.823625 0.729496 0.208691 0.011 Uiso 0.0998(16) 1 calc R U P A -2
Cl1 Cl 0.96871(6) 0.79546(4) 0.00171(3) 0.03159(15) Uani 0.9002(16) 1 d . . P A
-1
F1 F 1.1565(4) 0.5862(3) -0.0012(2) 0.0328(5) Uani 0.9002(16) 1 d . . P A -1
C5 C 1.0122(2) 0.43991(14) 0.27296(10) 0.0237(4) Uani 0.9002(16) 1 d G U P A -1
H5 H 1.020418 0.364580 0.330052 0.028 Uiso 0.9002(16) 1 calc R U P A -1
C4 C 1.0903(2) 0.45762(14) 0.17608(12) 0.0252(4) Uani 0.9002(16) 1 d G U P A -1
H4 H 1.151892 0.394386 0.166950 0.030 Uiso 0.9002(16) 1 calc R U P A -1
C3 C 1.0784(2) 0.56784(16) 0.09255(10) 0.0228(4) Uani 0.9002(16) 1 d G U P A -1
C2 C 0.9883(2) 0.66035(13) 0.10591(11) 0.0214(4) Uani 0.9002(16) 1 d G U P A -1
C1 C 0.9102(2) 0.64265(14) 0.20279(13) 0.0229(5) Uani 0.9002(16) 1 d G U P A -1
H1 H 0.848623 0.705877 0.211919 0.027 Uiso 0.9002(16) 1 calc R U P A -1
C6 C 0.9222(3) 0.53243(16) 0.28632(10) 0.0216(5) Uani 0.9002(16) 1 d G U P A -1
O6 O 0.2159(4) 0.7490(2) 0.5228(2) 0.0251(6) Uani 0.5 1 d . . P B -1
H6 H 0.322985 0.766020 0.512996 0.038 Uiso 0.5 1 calc R U P B -1
O4 O -0.1282(4) 1.2389(2) 0.4904(2) 0.0265(6) Uani 0.5 1 d . . P B -1
O5 O -0.3526(3) 1.1320(2) 0.47871(19) 0.0269(5) Uani 0.5 1 d . . P B -1
H5B H -0.407108 1.193475 0.474691 0.040 Uiso 0.5 1 calc R U P B -1
C26 C 0.1256(3) 0.84953(19) 0.5105(2) 0.0241(14) Uani 0.5 1 d G . P B -1
C27 C 0.1975(2) 0.9493(2) 0.5176(2) 0.0231(6) Uani 0.5 1 d G . P B -1
H27 H 0.316488 0.950769 0.528400 0.028 Uiso 0.5 1 calc R U P B -1
C28 C 0.0952(3) 1.04689(18) 0.50877(19) 0.0230(9) Uani 0.5 1 d G . P B -1
H28 H 0.144360 1.115068 0.513579 0.028 Uiso 0.5 1 calc R U P B -1
C23 C -0.0789(3) 1.04472(18) 0.4929(2) 0.0189(6) Uani 0.5 1 d G . P B -1
C24 C -0.1508(2) 0.9450(2) 0.48590(19) 0.0219(9) Uani 0.5 1 d G . P B -1
H24 H -0.269785 0.943484 0.475072 0.026 Uiso 0.5 1 calc R U P B -1
C25 C -0.0485(3) 0.84736(18) 0.4947(2) 0.0222(6) Uani 0.5 1 d G . P B -1
H25 H -0.097660 0.779183 0.489894 0.027 Uiso 0.5 1 calc R U P B -1
C29 C -0.1875(7) 1.1481(4) 0.4864(3) 0.0205(9) Uani 0.5 1 d . . P B -1


_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 C13 1.3511(19) . ?
O1 C22 1.4356(18) . ?
O2 C12 1.3534(19) . ?
O2 C15 1.4402(18) . ?
O3 C19 1.420(3) . ?
O3 C20 1.427(2) . ?
N1 H1B 0.8800 . ?
N1 H1A 0.8800 . ?
N1 C7 1.361(2) . ?
N1 C6A 1.502(12) . ?
N1 C6 1.4097(17) . ?
N2 C7 1.336(2) . ?
N2 C8 1.344(2) . ?
N3 C8 1.316(2) . ?
N3 C9 1.377(2) . ?
N4 C17 1.471(2) . ?
N4 C18 1.462(2) . ?
N4 C21 1.466(2) . ?
C7 C10 1.437(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.409(2) . ?
C9 C14 1.416(2) . ?
C10 C11 1.412(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.368(2) . ?
C12 C13 1.435(2) . ?
C13 C14 1.368(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.509(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.519(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.514(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.507(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1A C2A 1.704(12) . ?
F1A C3A 1.35(3) . ?
C6A C1A 1.3900 . ?
C6A C5A 1.3900 . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.3900 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
Cl1 C2 1.7219(15) . ?
F1 C3 1.348(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C5 C6 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 C2 1.3900 . ?
C2 C1 1.3900 . ?
C1 H1 0.9500 . ?
C1 C6 1.3900 . ?
O6 H6 0.8400 . ?
O6 C26 1.359(3) . ?
O4 C29 1.229(5) . ?
O5 H5B 0.8400 . ?
O5 C29 1.316(6) . ?
C26 C27 1.3900 . ?
C26 C25 1.3900 . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C28 C23 1.3900 . ?
C23 C24 1.3900 . ?
C23 C29 1.483(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C22 117.07(13) . . ?
C12 O2 C15 116.64(12) . . ?
C19 O3 C20 109.35(14) . . ?
C7 N1 H1B 114.2 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 C6A 120.0(6) . . ?
C7 N1 C6 131.61(14) . . ?
C6A N1 H1A 120.0 . . ?
C6 N1 H1B 114.2 . . ?
C7 N2 C8 116.58(14) . . ?
C8 N3 C9 116.63(14) . . ?
C18 N4 C17 108.86(13) . . ?
C18 N4 C21 108.80(14) . . ?
C21 N4 C17 111.97(14) . . ?
N1 C7 C10 119.14(14) . . ?
N2 C7 N1 119.33(14) . . ?
N2 C7 C10 121.52(14) . . ?
N2 C8 H8 116.1 . . ?
N3 C8 N2 127.90(15) . . ?
N3 C8 H8 116.1 . . ?
N3 C9 C10 120.88(14) . . ?
N3 C9 C14 119.09(14) . . ?
C10 C9 C14 120.02(14) . . ?
C9 C10 C7 116.34(14) . . ?
C9 C10 C11 119.20(14) . . ?
C11 C10 C7 124.45(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.61(14) . . ?
C12 C11 H11 119.7 . . ?
O2 C12 C11 125.09(14) . . ?
O2 C12 C13 114.89(13) . . ?
C11 C12 C13 120.02(14) . . ?
O1 C13 C12 114.29(14) . . ?
O1 C13 C14 125.59(14) . . ?
C14 C13 C12 120.13(14) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.01(14) . . ?
C13 C14 H14 120.0 . . ?
O2 C15 H15A 110.4 . . ?
O2 C15 H15B 110.4 . . ?
O2 C15 C16 106.79(13) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.4 . . ?
C16 C15 H15B 110.4 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.89(14) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
N4 C17 C16 114.07(14) . . ?
N4 C17 H17A 108.7 . . ?
N4 C17 H17B 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 C19 110.85(14) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
O3 C19 C18 111.47(18) . . ?
O3 C19 H19A 109.3 . . ?
O3 C19 H19B 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
O3 C20 H20A 109.4 . . ?
O3 C20 H20B 109.4 . . ?
O3 C20 C21 111.25(15) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
N4 C21 C20 109.80(16) . . ?
N4 C21 H21A 109.7 . . ?
N4 C21 H21B 109.7 . . ?
C20 C21 H21A 109.7 . . ?
C20 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1A C6A N1 109.2(9) . . ?
C1A C6A C5A 120.0 . . ?
C5A C6A N1 130.8(9) . . ?
C6A C1A H1AA 120.0 . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A H1AA 120.0 . . ?
C1A C2A Cl1A 115.8(9) . . ?
C3A C2A Cl1A 124.1(8) . . ?
C3A C2A C1A 120.0 . . ?
F1A C3A C2A 114.5(14) . . ?
F1A C3A C4A 125.5(14) . . ?
C2A C3A C4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
F1 C3 C4 120.22(15) . . ?
F1 C3 C2 119.76(15) . . ?
C4 C3 C2 120.0 . . ?
C3 C2 Cl1 119.93(9) . . ?
C3 C2 C1 120.0 . . ?
C1 C2 Cl1 120.05(9) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C6 C1 H1 120.0 . . ?
C5 C6 N1 116.84(11) . . ?
C1 C6 N1 123.15(11) . . ?
C1 C6 C5 120.0 . . ?
C26 O6 H6 109.5 . . ?
C29 O5 H5B 109.5 . . ?
O6 C26 C27 123.10(19) . . ?
O6 C26 C25 116.84(19) . . ?
C27 C26 C25 120.0 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.0 . . ?
C23 C28 C27 120.0 . . ?
C23 C28 H28 120.0 . . ?
C28 C23 C24 120.0 . . ?
C28 C23 C29 119.4(2) . . ?
C24 C23 C29 120.6(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
O4 C29 O5 123.6(4) . . ?
O4 C29 C23 122.6(5) . . ?
O5 C29 C23 113.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C9 178.74(14) . . . . ?
O2 C12 C13 O1 1.29(19) . . . . ?
O2 C12 C13 C14 -178.85(13) . . . . ?
O2 C15 C16 C17 67.29(17) . . . . ?
O3 C20 C21 N4 -60.0(2) . . . . ?
N1 C7 C10 C9 -176.94(13) . . . . ?
N1 C7 C10 C11 2.2(2) . . . . ?
N1 C6A C1A C2A 178.4(14) . . . . ?
N1 C6A C5A C4A -178.0(18) . . . . ?
N2 C7 C10 C9 2.8(2) . . . . ?
N2 C7 C10 C11 -178.04(14) . . . . ?
N3 C9 C10 C7 0.7(2) . . . . ?
N3 C9 C10 C11 -178.50(13) . . . . ?
N3 C9 C14 C13 178.96(14) . . . . ?
N4 C18 C19 O3 57.5(2) . . . . ?
C7 N1 C6A C1A 180.0(5) . . . . ?
C7 N1 C6A C5A -1.8(16) . . . . ?
C7 N1 C6 C5 178.63(14) . . . . ?
C7 N1 C6 C1 -0.2(3) . . . . ?
C7 N2 C8 N3 2.7(2) . . . . ?
C7 C10 C11 C12 -178.93(14) . . . . ?
C8 N2 C7 N1 175.39(14) . . . . ?
C8 N2 C7 C10 -4.3(2) . . . . ?
C8 N3 C9 C10 -2.4(2) . . . . ?
C8 N3 C9 C14 178.64(14) . . . . ?
C9 N3 C8 N2 0.7(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?
C10 C11 C12 O2 179.37(14) . . . . ?
C10 C11 C12 C13 -1.3(2) . . . . ?
C11 C12 C13 O1 -178.06(13) . . . . ?
C11 C12 C13 C14 1.8(2) . . . . ?
C12 O2 C15 C16 179.40(13) . . . . ?
C12 C13 C14 C9 -1.1(2) . . . . ?
C14 C9 C10 C7 179.70(13) . . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C15 O2 C12 C11 0.9(2) . . . . ?
C15 O2 C12 C13 -178.42(13) . . . . ?
C15 C16 C17 N4 60.75(19) . . . . ?
C17 N4 C18 C19 -178.16(15) . . . . ?
C17 N4 C21 C20 177.35(14) . . . . ?
C18 N4 C17 C16 -177.85(14) . . . . ?
C18 N4 C21 C20 56.98(19) . . . . ?
C19 O3 C20 C21 59.7(2) . . . . ?
C20 O3 C19 C18 -58.1(2) . . . . ?
C21 N4 C17 C16 61.82(18) . . . . ?
C21 N4 C18 C19 -55.9(2) . . . . ?
C22 O1 C13 C12 174.51(13) . . . . ?
C22 O1 C13 C14 -5.3(2) . . . . ?
Cl1A C2A C3A F1A -6(2) . . . . ?
Cl1A C2A C3A C4A 175.1(12) . . . . ?
F1A C3A C4A C5A -179(2) . . . . ?
C6A N1 C7 N2 -1.9(9) . . . . ?
C6A N1 C7 C10 177.8(9) . . . . ?
C6A C1A C2A Cl1A -175.5(11) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C1A C6A C5A C4A 0.0 . . . . ?
C1A C2A C3A F1A 179(2) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C5A C6A C1A C2A 0.0 . . . . ?
Cl1 C2 C1 C6 178.29(13) . . . . ?
F1 C3 C2 Cl1 2.9(2) . . . . ?
F1 C3 C2 C1 -178.8(2) . . . . ?
C5 C4 C3 F1 178.8(2) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C5 C6 N1 -178.90(18) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C3 C2 Cl1 -178.29(13) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C2 C1 C6 N1 178.83(19) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C6 N1 C7 N2 -0.8(3) . . . . ?
C6 N1 C7 C10 178.89(17) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
O6 C26 C27 C28 -177.1(3) . . . . ?
O6 C26 C25 C24 177.3(3) . . . . ?
C26 C27 C28 C23 0.0 . . . . ?
C27 C26 C25 C24 0.0 . . . . ?
C27 C28 C23 C24 0.0 . . . . ?
C27 C28 C23 C29 178.4(3) . . . . ?
C28 C23 C24 C25 0.0 . . . . ?
C28 C23 C29 O4 2.9(5) . . . . ?
C28 C23 C29 O5 -175.4(2) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C23 C29 O4 -178.7(3) . . . . ?
C24 C23 C29 O5 3.1(5) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C29 C23 C24 C25 -178.4(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_6261
_database_code_depnum_ccdc_archive 'CCDC 2322079'
loop_
_audit_author_name
_audit_author_address
'Ningbo Gong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 Cl F N4 O3, C10 H9 O4'
_chemical_formula_sum            'C32 H34 Cl F N4 O7'
_chemical_formula_weight         641.08
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.83646(5)
_cell_length_b                   26.10472(10)
_cell_length_c                   10.91005(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.9370(4)
_cell_angle_gamma                90
_cell_volume                     3039.96(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.764
_cell_measurement_theta_min      3.386
_shelx_estimated_absorpt_T_max   0.808
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995).  '
_exptl_absorpt_special_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40367
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.764
_diffrn_reflns_theta_min         3.386
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku 002+'
_diffrn_measurement_method       /w/k
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5487
_reflns_number_total             5795
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00045(7)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.039
_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)+(0.0536P)²+0.7565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4A), C5(H5), C8(H8), C11(H11), C14(H14), C23(H23),
 C26(H26), C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.37215(5) 0.61078(2) 0.84078(5) 0.07758(16) Uani 1 1 d . . . . .
F1 F 0.30300(10) 0.51384(5) 0.94994(10) 0.0768(3) Uani 1 1 d . . . . .
O1 O 1.02359(10) 0.45360(3) 0.24842(10) 0.0498(2) Uani 1 1 d . . . . .
O2 O 0.92120(10) 0.38608(3) 0.36431(10) 0.0485(2) Uani 1 1 d . . . . .
O3 O 1.00038(10) 0.10208(3) 0.43678(10) 0.0522(3) Uani 1 1 d . . . . .
N1 N 0.63137(10) 0.48613(4) 0.61915(11) 0.0416(2) Uani 1 1 d . . . . .
H1 H 0.649543 0.454390 0.610929 0.050 Uiso 1 1 calc R U . . .
N2 N 0.65872(12) 0.56897(4) 0.55194(12) 0.0505(3) Uani 1 1 d . . . . .
N3 N 0.79925(12) 0.58959(4) 0.41251(12) 0.0468(3) Uani 1 1 d . . . . .
N4 N 0.89189(10) 0.20191(4) 0.41843(10) 0.0350(2) Uani 1 1 d . . . . .
H4 H 0.825(2) 0.1996(8) 0.339(2) 0.081(6) Uiso 1 1 d . . . . .
C1 C 0.50595(14) 0.54459(6) 0.72794(14) 0.0482(3) Uani 1 1 d . . . . .
H1A H 0.531985 0.573216 0.688505 0.058 Uiso 1 1 calc R U . . .
C2 C 0.42418(14) 0.54989(6) 0.81165(14) 0.0522(4) Uani 1 1 d . . . . .
C3 C 0.38445(15) 0.50825(7) 0.87004(15) 0.0550(4) Uani 1 1 d . . . . .
C4 C 0.42728(16) 0.46016(7) 0.84776(15) 0.0577(4) Uani 1 1 d . . . . .
H4A H 0.401280 0.431844 0.888346 0.069 Uiso 1 1 calc R U . . .
C5 C 0.50897(14) 0.45411(6) 0.76497(14) 0.0508(3) Uani 1 1 d . . . . .
H5 H 0.537854 0.421532 0.750107 0.061 Uiso 1 1 calc R U . . .
C6 C 0.54885(12) 0.49601(5) 0.70332(12) 0.0410(3) Uani 1 1 d . . . . .
C7 C 0.68643(12) 0.51942(5) 0.54905(12) 0.0383(3) Uani 1 1 d . . . . .
C8 C 0.71702(16) 0.60039(5) 0.48329(16) 0.0545(4) Uani 1 1 d . . . . .
H8 H 0.695918 0.634834 0.486498 0.065 Uiso 1 1 calc R U . . .
C9 C 0.82771(12) 0.53828(5) 0.40595(12) 0.0383(3) Uani 1 1 d . . . . .
C10 C 0.77272(11) 0.50108(4) 0.47315(12) 0.0362(3) Uani 1 1 d . . . . .
C11 C 0.80454(12) 0.44898(5) 0.46158(12) 0.0390(3) Uani 1 1 d . . . . .
H11 H 0.769648 0.424138 0.506284 0.047 Uiso 1 1 calc R U . . .
C12 C 0.88609(12) 0.43487(4) 0.38531(12) 0.0390(3) Uani 1 1 d . . . . .
C13 C 0.94281(12) 0.47261(5) 0.31865(12) 0.0386(3) Uani 1 1 d . . . . .
C14 C 0.91330(13) 0.52314(5) 0.32939(12) 0.0405(3) Uani 1 1 d . . . . .
H14 H 0.950125 0.547755 0.285692 0.049 Uiso 1 1 calc R U . . .
C15 C 0.87372(14) 0.34679(5) 0.43372(14) 0.0456(3) Uani 1 1 d . . . . .
H15A H 0.783091 0.348766 0.422656 0.055 Uiso 1 1 calc R U . . .
H15B H 0.907414 0.350415 0.521609 0.055 Uiso 1 1 calc R U . . .
C16 C 0.91352(14) 0.29623(5) 0.38570(13) 0.0442(3) Uani 1 1 d . . . . .
H16A H 0.868230 0.290112 0.302256 0.053 Uiso 1 1 calc R U . . .
H16B H 1.002412 0.296915 0.382544 0.053 Uiso 1 1 calc R U . . .
C17 C 0.88580(14) 0.25408(5) 0.47175(12) 0.0417(3) Uani 1 1 d . . . . .
H17A H 0.945404 0.256203 0.548884 0.050 Uiso 1 1 calc R U . . .
H17B H 0.802787 0.259439 0.491362 0.050 Uiso 1 1 calc R U . . .
C18 C 0.86420(15) 0.16337(5) 0.51048(14) 0.0498(3) Uani 1 1 d . . . . .
H18A H 0.779317 0.168223 0.525476 0.060 Uiso 1 1 calc R U . . .
H18B H 0.920915 0.168297 0.588671 0.060 Uiso 1 1 calc R U . . .
C19 C 0.87844(15) 0.10961(5) 0.46394(16) 0.0529(4) Uani 1 1 d . . . . .
H19A H 0.863268 0.085191 0.526677 0.064 Uiso 1 1 calc R U . . .
H19B H 0.816905 0.103704 0.389514 0.064 Uiso 1 1 calc R U . . .
C20 C 1.02078(15) 0.13650(5) 0.34173(15) 0.0500(3) Uani 1 1 d . . . . .
H20A H 0.957613 0.130900 0.268403 0.060 Uiso 1 1 calc R U . . .
H20B H 1.102111 0.129730 0.319466 0.060 Uiso 1 1 calc R U . . .
C21 C 1.01547(12) 0.19159(5) 0.38280(13) 0.0405(3) Uani 1 1 d . . . . .
H21A H 1.081578 0.198001 0.453174 0.049 Uiso 1 1 calc R U . . .
H21B H 1.028001 0.214237 0.315539 0.049 Uiso 1 1 calc R U . . .
C22 C 1.08031(16) 0.48888(6) 0.17566(15) 0.0544(4) Uani 1 1 d . . . . .
H22A H 1.016427 0.506124 0.118513 0.082 Uiso 1 1 calc R U . . .
H22B H 1.134752 0.470737 0.130033 0.082 Uiso 1 1 calc R U . . .
H22C H 1.128010 0.513580 0.229351 0.082 Uiso 1 1 calc R U . . .
O4 O 0.16609(10) 0.30343(4) -0.36629(10) 0.0525(3) Uani 1 1 d . . . . .
H4B H 0.166980 0.334798 -0.369829 0.079 Uiso 1 1 calc R U . . .
O5 O 0.19555(14) 0.20349(4) -0.33276(13) 0.0812(5) Uani 1 1 d . . . . .
O6 O 0.70284(10) 0.12426(4) 0.17037(10) 0.0533(3) Uani 1 1 d . . . . .
O7 O 0.72782(11) 0.20698(4) 0.21894(11) 0.0603(3) Uani 1 1 d . . . . .
C23 C 0.36778(14) 0.21646(6) -0.16158(14) 0.0507(3) Uani 1 1 d . . . . .
H23 H 0.378980 0.181334 -0.150571 0.061 Uiso 1 1 calc R U . . .
C24 C 0.27576(14) 0.23435(6) -0.25544(14) 0.0495(3) Uani 1 1 d . . . . .
C25 C 0.25985(13) 0.28710(5) -0.27486(13) 0.0442(3) Uani 1 1 d . . . . .
C26 C 0.33770(15) 0.32016(6) -0.20032(17) 0.0581(4) Uani 1 1 d . . . . .
H26 H 0.329709 0.355250 -0.214153 0.070 Uiso 1 1 calc R U . . .
C27 C 0.42805(16) 0.30200(6) -0.10471(18) 0.0632(5) Uani 1 1 d . . . . .
H27 H 0.478707 0.325143 -0.054272 0.076 Uiso 1 1 calc R U . . .
C28 C 0.44419(13) 0.25006(6) -0.08303(14) 0.0493(3) Uani 1 1 d . . . . .
C29 C 0.53932(14) 0.23175(6) 0.01997(15) 0.0514(3) Uani 1 1 d . . . . .
H29 H 0.579015 0.256870 0.073100 0.062 Uiso 1 1 calc R U . . .
C30 C 0.57581(13) 0.18413(6) 0.04692(13) 0.0469(3) Uani 1 1 d . . . . .
H30 H 0.537216 0.157928 -0.003407 0.056 Uiso 1 1 calc R U . . .
C31 C 0.67520(13) 0.17023(5) 0.15332(13) 0.0430(3) Uani 1 1 d . . . . .
C32 C 0.2161(3) 0.14972(7) -0.3189(3) 0.1380(15) Uani 1 1 d . . . . .
H32A H 0.160374 0.131890 -0.382761 0.207 Uiso 1 1 calc R U . . .
H32B H 0.200687 0.139058 -0.238748 0.207 Uiso 1 1 calc R U . . .
H32C H 0.301254 0.142004 -0.325993 0.207 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 C2 1.7342(15) . ?
F1 C3 1.3511(18) . ?
O1 C13 1.3531(16) . ?
O1 C22 1.4227(17) . ?
O2 C12 1.3600(14) . ?
O2 C15 1.4228(16) . ?
O3 C19 1.417(2) . ?
O3 C20 1.4181(18) . ?
N1 H1 0.8600 . ?
N1 C6 1.4116(17) . ?
N1 C7 1.3614(17) . ?
N2 C7 1.3296(16) . ?
N2 C8 1.340(2) . ?
N3 C8 1.307(2) . ?
N3 C9 1.3791(16) . ?
N4 H4 1.03(2) . ?
N4 C17 1.4869(15) . ?
N4 C18 1.4882(16) . ?
N4 C21 1.4822(17) . ?
C1 H1A 0.9300 . ?
C1 C2 1.385(2) . ?
C1 C6 1.3928(19) . ?
C2 C3 1.367(2) . ?
C3 C4 1.374(2) . ?
C4 H4A 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(2) . ?
C7 C10 1.4341(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.4094(18) . ?
C9 C14 1.4077(19) . ?
C10 C11 1.4141(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3648(19) . ?
C12 C13 1.4253(18) . ?
C13 C14 1.3673(17) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5102(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5097(18) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.509(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.5102(18) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O4 H4B 0.8200 . ?
O4 C25 1.3636(16) . ?
O5 C24 1.3650(17) . ?
O5 C32 1.425(2) . ?
O6 C31 1.2432(17) . ?
O7 C31 1.2716(17) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(2) . ?
C23 C28 1.394(2) . ?
C24 C25 1.399(2) . ?
C25 C26 1.372(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.382(2) . ?
C28 C29 1.468(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.322(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.4857(19) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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
C13 O1 C22 117.55(11) . . ?
C12 O2 C15 116.62(10) . . ?
C19 O3 C20 109.50(11) . . ?
C6 N1 H1 115.2 . . ?
C7 N1 H1 115.2 . . ?
C7 N1 C6 129.58(11) . . ?
C7 N2 C8 116.87(12) . . ?
C8 N3 C9 114.93(12) . . ?
C17 N4 H4 107.9(12) . . ?
C17 N4 C18 109.11(10) . . ?
C18 N4 H4 109.4(12) . . ?
C21 N4 H4 107.9(12) . . ?
C21 N4 C17 111.85(10) . . ?
C21 N4 C18 110.52(10) . . ?
C2 C1 H1A 120.3 . . ?
C2 C1 C6 119.40(14) . . ?
C6 C1 H1A 120.3 . . ?
C1 C2 Cl1 118.54(13) . . ?
C3 C2 Cl1 120.34(12) . . ?
C3 C2 C1 121.12(14) . . ?
F1 C3 C2 120.54(15) . . ?
F1 C3 C4 119.40(16) . . ?
C2 C3 C4 120.06(14) . . ?
C3 C4 H4A 120.2 . . ?
C3 C4 C5 119.68(15) . . ?
C5 C4 H4A 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.98(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 N1 124.17(13) . . ?
C5 C6 N1 117.09(12) . . ?
C5 C6 C1 118.74(13) . . ?
N1 C7 C10 120.26(11) . . ?
N2 C7 N1 119.01(12) . . ?
N2 C7 C10 120.72(12) . . ?
N2 C8 H8 115.3 . . ?
N3 C8 N2 129.32(13) . . ?
N3 C8 H8 115.3 . . ?
N3 C9 C10 121.59(12) . . ?
N3 C9 C14 118.66(12) . . ?
C14 C9 C10 119.75(11) . . ?
C9 C10 C7 116.53(11) . . ?
C9 C10 C11 119.00(12) . . ?
C11 C10 C7 124.47(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.49(12) . . ?
C12 C11 H11 119.8 . . ?
O2 C12 C11 125.79(12) . . ?
O2 C12 C13 113.80(11) . . ?
C11 C12 C13 120.41(11) . . ?
O1 C13 C12 114.43(11) . . ?
O1 C13 C14 125.87(12) . . ?
C14 C13 C12 119.69(12) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.63(12) . . ?
C13 C14 H14 119.7 . . ?
O2 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
O2 C15 C16 107.11(11) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 C15 108.77(11) . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
N4 C17 C16 113.40(10) . . ?
N4 C17 H17A 108.9 . . ?
N4 C17 H17B 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 C19 110.93(12) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
O3 C19 C18 110.64(12) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
O3 C20 H20A 109.3 . . ?
O3 C20 H20B 109.3 . . ?
O3 C20 C21 111.57(12) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
N4 C21 C20 109.47(11) . . ?
N4 C21 H21A 109.8 . . ?
N4 C21 H21B 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 O4 H4B 109.5 . . ?
C24 O5 C32 116.39(13) . . ?
C24 C23 H23 119.4 . . ?
C24 C23 C28 121.26(13) . . ?
C28 C23 H23 119.4 . . ?
O5 C24 C23 124.04(13) . . ?
O5 C24 C25 116.01(12) . . ?
C23 C24 C25 119.95(13) . . ?
O4 C25 C24 118.37(12) . . ?
O4 C25 C26 122.78(13) . . ?
C26 C25 C24 118.84(13) . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 120.90(14) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.11(14) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 C29 122.00(13) . . ?
C27 C28 C23 117.88(13) . . ?
C27 C28 C29 120.12(13) . . ?
C28 C29 H29 115.8 . . ?
C30 C29 C28 128.32(14) . . ?
C30 C29 H29 115.8 . . ?
C29 C30 H30 118.2 . . ?
C29 C30 C31 123.50(13) . . ?
C31 C30 H30 118.2 . . ?
O6 C31 O7 124.82(13) . . ?
O6 C31 C30 118.43(12) . . ?
O7 C31 C30 116.74(12) . . ?
O5 C32 H32A 109.5 . . ?
O5 C32 H32B 109.5 . . ?
O5 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
Cl1 C2 C3 F1 0.8(2) . . . . ?
Cl1 C2 C3 C4 -179.17(13) . . . . ?
F1 C3 C4 C5 179.06(14) . . . . ?
O1 C13 C14 C9 -179.85(12) . . . . ?
O2 C12 C13 O1 -1.39(17) . . . . ?
O2 C12 C13 C14 178.57(12) . . . . ?
O2 C15 C16 C17 169.79(12) . . . . ?
O3 C20 C21 N4 -58.27(15) . . . . ?
N1 C7 C10 C9 -178.50(11) . . . . ?
N1 C7 C10 C11 1.86(19) . . . . ?
N2 C7 C10 C9 1.66(18) . . . . ?
N2 C7 C10 C11 -177.98(13) . . . . ?
N3 C9 C10 C7 -0.37(18) . . . . ?
N3 C9 C10 C11 179.30(12) . . . . ?
N3 C9 C14 C13 -179.02(12) . . . . ?
N4 C18 C19 O3 56.92(17) . . . . ?
C1 C2 C3 F1 -178.88(14) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C1 C6 N1 179.47(12) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 N1 -179.28(13) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C6 N1 C7 N2 -3.1(2) . . . . ?
C6 N1 C7 C10 177.09(12) . . . . ?
C6 C1 C2 Cl1 179.98(11) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 N1 C6 C1 1.3(2) . . . . ?
C7 N1 C6 C5 -178.54(13) . . . . ?
C7 N2 C8 N3 -0.3(3) . . . . ?
C7 C10 C11 C12 178.83(12) . . . . ?
C8 N2 C7 N1 178.76(13) . . . . ?
C8 N2 C7 C10 -1.4(2) . . . . ?
C8 N3 C9 C10 -1.1(2) . . . . ?
C8 N3 C9 C14 178.53(13) . . . . ?
C9 N3 C8 N2 1.5(3) . . . . ?
C9 C10 C11 C12 -0.80(19) . . . . ?
C10 C9 C14 C13 0.60(19) . . . . ?
C10 C11 C12 O2 -178.26(12) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 O1 178.73(12) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C12 O2 C15 C16 174.22(12) . . . . ?
C12 C13 C14 C9 0.2(2) . . . . ?
C14 C9 C10 C7 -179.97(11) . . . . ?
C14 C9 C10 C11 -0.30(18) . . . . ?
C15 O2 C12 C11 -3.7(2) . . . . ?
C15 O2 C12 C13 176.38(12) . . . . ?
C15 C16 C17 N4 165.99(12) . . . . ?
C17 N4 C18 C19 -175.94(12) . . . . ?
C17 N4 C21 C20 174.26(11) . . . . ?
C18 N4 C17 C16 179.57(12) . . . . ?
C18 N4 C21 C20 52.48(15) . . . . ?
C19 O3 C20 C21 62.74(16) . . . . ?
C20 O3 C19 C18 -61.36(16) . . . . ?
C21 N4 C17 C16 56.98(15) . . . . ?
C21 N4 C18 C19 -52.55(16) . . . . ?
C22 O1 C13 C12 177.75(12) . . . . ?
C22 O1 C13 C14 -2.2(2) . . . . ?
O4 C25 C26 C27 176.97(16) . . . . ?
O5 C24 C25 O4 1.0(2) . . . . ?
O5 C24 C25 C26 -179.88(16) . . . . ?
C23 C24 C25 O4 -178.38(14) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C23 C28 C29 C30 7.2(3) . . . . ?
C24 C23 C28 C27 -2.3(3) . . . . ?
C24 C23 C28 C29 177.73(15) . . . . ?
C24 C25 C26 C27 -2.1(3) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C26 C27 C28 C23 0.9(3) . . . . ?
C26 C27 C28 C29 -179.11(17) . . . . ?
C27 C28 C29 C30 -172.84(18) . . . . ?
C28 C23 C24 O5 -177.89(17) . . . . ?
C28 C23 C24 C25 1.5(3) . . . . ?
C28 C29 C30 C31 178.99(15) . . . . ?
C29 C30 C31 O6 -179.77(15) . . . . ?
C29 C30 C31 O7 -1.3(2) . . . . ?
C32 O5 C24 C23 -4.5(3) . . . . ?
C32 O5 C24 C25 176.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6275
_database_code_depnum_ccdc_archive 'CCDC 2322081'
loop_
_audit_author_name
_audit_author_address
'Ningbo Gong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2021-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 Cl F N4 O3, C7 H3 N2 O6, C7 H4 N2 O6'
_chemical_formula_sum            'C36 H32 Cl F N8 O15'
_chemical_formula_weight         871.14
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.38070(10)
_cell_length_b                   22.4116(2)
_cell_length_c                   23.00200(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.1950(10)
_cell_angle_gamma                90
_cell_volume                     3789.21(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6327
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.332
_cell_measurement_theta_min      2.758
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995).  '
_exptl_absorpt_special_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32511
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.332
_diffrn_reflns_theta_min         2.758
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku 002+'
_diffrn_measurement_method       /w/k
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6327
_reflns_number_total             7281
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00099(9)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.050
_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)+(0.0575P)²+0.8604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4A), C5(H5), C8(H8), C11(H11), C14(H14), C24(H24),
 C26(H26), C28(H28), C31(H31), C33(H33), C35(H35)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O11(H11A)
;
_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 0.16860(7) 0.15467(3) 0.25383(2) 0.06458(16) Uani 1 1 d . . . . .
F1 F 0.52898(19) 0.11960(7) 0.22904(5) 0.0792(4) Uani 1 1 d . . . . .
O1 O 0.32403(18) 0.39228(5) 0.65827(5) 0.0497(3) Uani 1 1 d . . . . .
O2 O 0.37130(17) 0.27989(5) 0.65693(5) 0.0468(3) Uani 1 1 d . . . . .
O3 O 0.9590(2) 0.06844(6) 0.77398(6) 0.0607(3) Uani 1 1 d . . . . .
N1 N 0.5194(2) 0.23055(6) 0.44242(5) 0.0453(3) Uani 1 1 d . . . . .
H1 H 0.539026 0.208696 0.473078 0.054 Uiso 1 1 calc R U . . .
N2 N 0.4895(2) 0.32319(6) 0.40099(6) 0.0487(3) Uani 1 1 d . . . . .
N3 N 0.4061(2) 0.40729(6) 0.45430(6) 0.0478(3) Uani 1 1 d . . . . .
N4 N 0.61018(19) 0.11525(6) 0.73117(5) 0.0408(3) Uani 1 1 d . . . . .
H4 H 0.623058 0.114431 0.689143 0.049 Uiso 1 1 calc R U . . .
C1 C 0.3643(2) 0.19466(7) 0.35194(7) 0.0432(4) Uani 1 1 d . . . . .
H1A H 0.254831 0.207227 0.364900 0.052 Uiso 1 1 calc R U . . .
C2 C 0.3662(2) 0.16695(7) 0.29832(7) 0.0429(4) Uani 1 1 d . . . . .
C3 C 0.5300(3) 0.14872(8) 0.28013(7) 0.0497(4) Uani 1 1 d . . . . .
C4 C 0.6902(3) 0.15795(10) 0.31327(9) 0.0584(5) Uani 1 1 d . . . . .
H4A H 0.799544 0.145818 0.299886 0.070 Uiso 1 1 calc R U . . .
C5 C 0.6884(3) 0.18563(8) 0.36714(8) 0.0512(4) Uani 1 1 d . . . . .
H5 H 0.796648 0.192025 0.390274 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5253(2) 0.20361(6) 0.38617(6) 0.0401(3) Uani 1 1 d . . . . .
C7 C 0.4843(2) 0.28880(7) 0.44880(6) 0.0384(3) Uani 1 1 d . . . . .
C8 C 0.4487(3) 0.38062(7) 0.40682(7) 0.0518(4) Uani 1 1 d . . . . .
H8 H 0.450647 0.404255 0.373654 0.062 Uiso 1 1 calc R U . . .
C9 C 0.4040(2) 0.37407(6) 0.50447(6) 0.0382(3) Uani 1 1 d . . . . .
C10 C 0.4441(2) 0.31298(6) 0.50380(6) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.4357(2) 0.27957(6) 0.55560(6) 0.0367(3) Uani 1 1 d . . . . .
H11 H 0.460237 0.238867 0.555832 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3912(2) 0.30729(7) 0.60546(6) 0.0367(3) Uani 1 1 d . . . . .
C13 C 0.3575(2) 0.37009(7) 0.60609(6) 0.0376(3) Uani 1 1 d . . . . .
C14 C 0.3613(2) 0.40254(7) 0.55583(7) 0.0405(3) Uani 1 1 d . . . . .
H14 H 0.335701 0.443179 0.555708 0.049 Uiso 1 1 calc R U . . .
C15 C 0.4185(2) 0.21840(7) 0.66233(7) 0.0429(4) Uani 1 1 d . . . . .
H15A H 0.544242 0.212197 0.654679 0.051 Uiso 1 1 calc R U . . .
H15B H 0.340979 0.194468 0.635158 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3903(2) 0.20210(7) 0.72461(7) 0.0455(4) Uani 1 1 d . . . . .
H16A H 0.471325 0.226217 0.750555 0.055 Uiso 1 1 calc R U . . .
H16B H 0.266584 0.212234 0.731841 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4229(2) 0.13721(8) 0.73977(7) 0.0458(4) Uani 1 1 d . . . . .
H17A H 0.400638 0.131153 0.780273 0.055 Uiso 1 1 calc R U . . .
H17B H 0.335319 0.113243 0.716000 0.055 Uiso 1 1 calc R U . . .
C18 C 0.7574(2) 0.15378(7) 0.75947(7) 0.0462(4) Uani 1 1 d . . . . .
H18A H 0.742433 0.157573 0.800768 0.055 Uiso 1 1 calc R U . . .
H18B H 0.749297 0.193312 0.742270 0.055 Uiso 1 1 calc R U . . .
C19 C 0.9409(3) 0.12727(10) 0.75167(9) 0.0606(5) Uani 1 1 d . . . . .
H19A H 0.959312 0.126829 0.710449 0.073 Uiso 1 1 calc R U . . .
H19B H 1.034629 0.152247 0.771414 0.073 Uiso 1 1 calc R U . . .
C20 C 0.8232(3) 0.03070(9) 0.74574(8) 0.0642(5) Uani 1 1 d . . . . .
H20A H 0.837848 -0.009384 0.761366 0.077 Uiso 1 1 calc R U . . .
H20B H 0.838607 0.029011 0.704336 0.077 Uiso 1 1 calc R U . . .
C21 C 0.6355(3) 0.05281(7) 0.75415(8) 0.0526(4) Uani 1 1 d . . . . .
H21A H 0.616835 0.052111 0.795354 0.063 Uiso 1 1 calc R U . . .
H21B H 0.546001 0.026704 0.733823 0.063 Uiso 1 1 calc R U . . .
C22 C 0.2931(3) 0.45524(8) 0.66215(9) 0.0585(5) Uani 1 1 d . . . . .
H22A H 0.184343 0.465660 0.638238 0.088 Uiso 1 1 calc R U . . .
H22B H 0.394617 0.476408 0.648845 0.088 Uiso 1 1 calc R U . . .
H22C H 0.279658 0.465820 0.701976 0.088 Uiso 1 1 calc R U . . .
O4 O 0.5953(3) 0.03118(8) 0.35196(6) 0.0898(6) Uani 1 1 d . . . . .
O5 O 0.8020(3) -0.03699(10) 0.35129(7) 0.0995(6) Uani 1 1 d . . . . .
O6 O 0.5751(3) 0.14636(6) 0.53516(6) 0.0730(5) Uani 1 1 d . . . . .
O7 O 0.6273(2) 0.09481(6) 0.61709(5) 0.0633(4) Uani 1 1 d . . . . .
O8 O 0.9427(3) -0.09485(7) 0.61320(8) 0.0797(5) Uani 1 1 d . . . . .
O9 O 0.9140(3) -0.14686(7) 0.53541(10) 0.1018(7) Uani 1 1 d . . . . .
N6 N 0.8981(2) -0.10068(7) 0.56162(8) 0.0593(4) Uani 1 1 d . . . . .
N29 N 0.7078(3) -0.00230(9) 0.37631(7) 0.0659(5) Uani 1 1 d . . . . .
C23 C 0.7309(2) -0.00158(8) 0.44048(7) 0.0461(4) Uani 1 1 d . . . . .
C24 C 0.6752(2) 0.04846(7) 0.46933(7) 0.0413(3) Uani 1 1 d . . . . .
H24 H 0.626508 0.081110 0.448423 0.050 Uiso 1 1 calc R U . . .
C25 C 0.6932(2) 0.04919(7) 0.52981(6) 0.0374(3) Uani 1 1 d . . . . .
C26 C 0.7667(2) -0.00007(7) 0.55980(7) 0.0410(3) Uani 1 1 d . . . . .
H26 H 0.780123 -0.000207 0.600392 0.049 Uiso 1 1 calc R U . . .
C27 C 0.8201(2) -0.04897(7) 0.52896(8) 0.0442(4) Uani 1 1 d . . . . .
C28 C 0.8035(2) -0.05117(8) 0.46869(8) 0.0488(4) Uani 1 1 d . . . . .
H28 H 0.839580 -0.084380 0.448415 0.059 Uiso 1 1 calc R U . . .
C29 C 0.6276(2) 0.10227(7) 0.56354(7) 0.0432(4) Uani 1 1 d . . . . .
O10 O 0.2373(2) 0.53405(6) 0.37233(5) 0.0665(4) Uani 1 1 d . . . . .
O11 O 0.2677(3) 0.50819(6) 0.46570(6) 0.0792(5) Uani 1 1 d . . . . .
H11A H 0.316051 0.478338 0.453461 0.095 Uiso 1 1 calc R U . . .
O12 O 0.0329(4) 0.62458(9) 0.61203(7) 0.1036(7) Uani 1 1 d . . . . .
O13 O -0.0371(3) 0.71661(8) 0.59814(8) 0.0876(5) Uani 1 1 d . . . . .
O14 O 0.1015(3) 0.75042(8) 0.33902(8) 0.0861(5) Uani 1 1 d . . . . .
O15 O -0.0069(3) 0.80223(6) 0.40597(8) 0.0826(5) Uani 1 1 d . . . . .
N7 N 0.0147(3) 0.66873(8) 0.58127(7) 0.0611(4) Uani 1 1 d . . . . .
N8 N 0.0561(2) 0.75626(7) 0.38803(8) 0.0570(4) Uani 1 1 d . . . . .
C30 C 0.1542(2) 0.60266(7) 0.44383(6) 0.0389(3) Uani 1 1 d . . . . .
C31 C 0.1148(2) 0.60885(7) 0.50151(7) 0.0437(4) Uani 1 1 d . . . . .
H31 H 0.127194 0.576614 0.527025 0.052 Uiso 1 1 calc R U . . .
C32 C 0.0571(2) 0.66342(7) 0.52029(7) 0.0440(4) Uani 1 1 d . . . . .
C33 C 0.0364(2) 0.71274(7) 0.48452(8) 0.0461(4) Uani 1 1 d . . . . .
H33 H -0.002620 0.749282 0.497939 0.055 Uiso 1 1 calc R U . . .
C34 C 0.0767(2) 0.70473(7) 0.42774(7) 0.0421(3) Uani 1 1 d . . . . .
C35 C 0.1340(2) 0.65090(7) 0.40623(7) 0.0398(3) Uani 1 1 d . . . . .
H35 H 0.158331 0.647239 0.367423 0.048 Uiso 1 1 calc R U . . .
C36 C 0.2234(2) 0.54356(7) 0.42326(7) 0.0452(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7264(18) . ?
F1 C3 1.3435(19) . ?
O1 C13 1.3428(18) . ?
O1 C22 1.433(2) . ?
O2 C12 1.3534(18) . ?
O2 C15 1.4241(19) . ?
O3 C19 1.417(3) . ?
O3 C20 1.423(3) . ?
N1 H1 0.8600 . ?
N1 C6 1.4320(19) . ?
N1 C7 1.342(2) . ?
N2 C7 1.346(2) . ?
N2 C8 1.331(2) . ?
N3 C8 1.308(2) . ?
N3 C9 1.375(2) . ?
N4 H4 0.9800 . ?
N4 C17 1.497(2) . ?
N4 C18 1.491(2) . ?
N4 C21 1.502(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.382(2) . ?
C1 C6 1.379(2) . ?
C2 C3 1.376(2) . ?
C3 C4 1.364(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(2) . ?
C7 C10 1.432(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.401(2) . ?
C9 C14 1.404(2) . ?
C10 C11 1.413(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(2) . ?
C12 C13 1.429(2) . ?
C13 C14 1.368(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.511(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.510(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.504(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.501(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O4 N29 1.217(3) . ?
O5 N29 1.222(3) . ?
O6 C29 1.227(2) . ?
O7 C29 1.243(2) . ?
O8 N6 1.209(2) . ?
O9 N6 1.209(2) . ?
N6 C27 1.470(2) . ?
N29 C23 1.470(2) . ?
C23 C24 1.384(2) . ?
C23 C28 1.371(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(2) . ?
C25 C26 1.386(2) . ?
C25 C29 1.523(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.382(2) . ?
C27 C28 1.381(3) . ?
C28 H28 0.9300 . ?
O10 C36 1.204(2) . ?
O11 H11A 0.8200 . ?
O11 C36 1.277(2) . ?
O12 N7 1.217(3) . ?
O13 N7 1.214(2) . ?
O14 N8 1.212(2) . ?
O15 N8 1.217(2) . ?
N7 C32 1.469(2) . ?
N8 C34 1.472(2) . ?
C30 C31 1.391(2) . ?
C30 C35 1.384(2) . ?
C30 C36 1.511(2) . ?
C31 H31 0.9300 . ?
C31 C32 1.377(2) . ?
C32 C33 1.378(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.377(2) . ?
C34 C35 1.385(2) . ?
C35 H35 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
C13 O1 C22 117.61(13) . . ?
C12 O2 C15 118.05(11) . . ?
C19 O3 C20 110.40(15) . . ?
C6 N1 H1 119.0 . . ?
C7 N1 H1 119.0 . . ?
C7 N1 C6 122.08(13) . . ?
C8 N2 C7 116.60(14) . . ?
C8 N3 C9 118.38(13) . . ?
C17 N4 H4 108.0 . . ?
C17 N4 C21 110.27(13) . . ?
C18 N4 H4 108.0 . . ?
C18 N4 C17 113.41(13) . . ?
C18 N4 C21 108.88(13) . . ?
C21 N4 H4 108.0 . . ?
C2 C1 H1A 120.1 . . ?
C6 C1 H1A 120.1 . . ?
C6 C1 C2 119.80(15) . . ?
C1 C2 Cl1 121.63(13) . . ?
C3 C2 Cl1 119.37(13) . . ?
C3 C2 C1 119.00(16) . . ?
F1 C3 C2 118.34(17) . . ?
F1 C3 C4 119.89(16) . . ?
C4 C3 C2 121.73(15) . . ?
C3 C4 H4A 120.3 . . ?
C3 C4 C5 119.30(16) . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.59(17) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 N1 118.83(14) . . ?
C5 C6 N1 120.59(16) . . ?
C5 C6 C1 120.55(14) . . ?
N1 C7 N2 116.60(13) . . ?
N1 C7 C10 121.50(13) . . ?
N2 C7 C10 121.91(13) . . ?
N2 C8 H8 116.6 . . ?
N3 C8 N2 126.83(15) . . ?
N3 C8 H8 116.6 . . ?
N3 C9 C10 120.10(13) . . ?
N3 C9 C14 118.75(13) . . ?
C10 C9 C14 121.15(14) . . ?
C9 C10 C7 116.13(13) . . ?
C9 C10 C11 118.88(13) . . ?
C11 C10 C7 124.94(13) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.84(13) . . ?
C12 C11 H11 120.1 . . ?
O2 C12 C11 125.43(13) . . ?
O2 C12 C13 113.90(12) . . ?
C11 C12 C13 120.66(13) . . ?
O1 C13 C12 114.83(13) . . ?
O1 C13 C14 125.30(14) . . ?
C14 C13 C12 119.87(13) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.52(14) . . ?
C13 C14 H14 120.2 . . ?
O2 C15 H15A 110.7 . . ?
O2 C15 H15B 110.7 . . ?
O2 C15 C16 105.25(12) . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C15 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 114.78(13) . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
N4 C17 C16 114.55(13) . . ?
N4 C17 H17A 108.6 . . ?
N4 C17 H17B 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
N4 C18 H18A 109.6 . . ?
N4 C18 H18B 109.6 . . ?
N4 C18 C19 110.35(15) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
O3 C19 C18 112.37(16) . . ?
O3 C19 H19A 109.1 . . ?
O3 C19 H19B 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
O3 C20 H20A 109.3 . . ?
O3 C20 H20B 109.3 . . ?
O3 C20 C21 111.43(15) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
N4 C21 H21A 109.6 . . ?
N4 C21 H21B 109.6 . . ?
C20 C21 N4 110.43(16) . . ?
C20 C21 H21A 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8 N6 C27 118.39(16) . . ?
O9 N6 O8 123.48(19) . . ?
O9 N6 C27 118.12(19) . . ?
O4 N29 O5 124.71(19) . . ?
O4 N29 C23 117.86(18) . . ?
O5 N29 C23 117.4(2) . . ?
C24 C23 N29 118.53(17) . . ?
C28 C23 N29 118.10(16) . . ?
C28 C23 C24 123.36(15) . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 119.04(15) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C26 119.19(14) . . ?
C24 C25 C29 120.99(14) . . ?
C26 C25 C29 119.78(13) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.54(15) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 N6 118.66(16) . . ?
C28 C27 N6 118.66(15) . . ?
C28 C27 C26 122.68(16) . . ?
C23 C28 C27 116.18(15) . . ?
C23 C28 H28 121.9 . . ?
C27 C28 H28 121.9 . . ?
O6 C29 O7 127.30(15) . . ?
O6 C29 C25 117.23(14) . . ?
O7 C29 C25 115.42(14) . . ?
C36 O11 H11A 109.5 . . ?
O12 N7 C32 117.86(16) . . ?
O13 N7 O12 123.64(17) . . ?
O13 N7 C32 118.50(18) . . ?
O14 N8 O15 123.56(17) . . ?
O14 N8 C34 118.09(16) . . ?
O15 N8 C34 118.35(17) . . ?
C31 C30 C36 119.48(14) . . ?
C35 C30 C31 119.89(14) . . ?
C35 C30 C36 120.62(14) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 C30 119.02(15) . . ?
C32 C31 H31 120.5 . . ?
C31 C32 N7 118.04(15) . . ?
C31 C32 C33 123.07(15) . . ?
C33 C32 N7 118.88(15) . . ?
C32 C33 H33 122.0 . . ?
C34 C33 C32 116.09(14) . . ?
C34 C33 H33 122.0 . . ?
C33 C34 N8 117.86(15) . . ?
C33 C34 C35 123.47(15) . . ?
C35 C34 N8 118.67(15) . . ?
C30 C35 C34 118.45(14) . . ?
C30 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
O10 C36 O11 126.54(16) . . ?
O10 C36 C30 121.39(15) . . ?
O11 C36 C30 112.03(14) . . ?

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 C2 C3 F1 -2.7(2) . . . . ?
Cl1 C2 C3 C4 179.23(16) . . . . ?
F1 C3 C4 C5 -177.05(18) . . . . ?
O1 C13 C14 C9 177.91(15) . . . . ?
O2 C12 C13 O1 4.3(2) . . . . ?
O2 C12 C13 C14 -175.74(15) . . . . ?
O2 C15 C16 C17 176.86(15) . . . . ?
O3 C20 C21 N4 58.10(19) . . . . ?
N1 C7 C10 C9 -177.99(16) . . . . ?
N1 C7 C10 C11 -0.4(3) . . . . ?
N2 C7 C10 C9 2.2(2) . . . . ?
N2 C7 C10 C11 179.72(16) . . . . ?
N3 C9 C10 C7 -0.5(2) . . . . ?
N3 C9 C10 C11 -178.18(15) . . . . ?
N3 C9 C14 C13 179.64(15) . . . . ?
N4 C18 C19 O3 -57.0(2) . . . . ?
C1 C2 C3 F1 177.22(16) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C1 C6 N1 -177.88(14) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 N1 177.99(17) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 N1 C7 N2 -12.4(2) . . . . ?
C6 N1 C7 C10 167.72(15) . . . . ?
C6 C1 C2 Cl1 179.98(13) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C7 N1 C6 C1 -73.0(2) . . . . ?
C7 N1 C6 C5 108.5(2) . . . . ?
C7 N2 C8 N3 0.8(3) . . . . ?
C7 C10 C11 C12 -178.34(15) . . . . ?
C8 N2 C7 N1 177.82(17) . . . . ?
C8 N2 C7 C10 -2.3(3) . . . . ?
C8 N3 C9 C10 -0.9(3) . . . . ?
C8 N3 C9 C14 179.00(17) . . . . ?
C9 N3 C8 N2 0.8(3) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C10 C9 C14 C13 -0.4(2) . . . . ?
C10 C11 C12 O2 177.07(15) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C11 C12 C13 O1 -176.89(15) . . . . ?
C11 C12 C13 C14 3.0(2) . . . . ?
C12 O2 C15 C16 177.33(14) . . . . ?
C12 C13 C14 C9 -2.0(2) . . . . ?
C14 C9 C10 C7 179.58(15) . . . . ?
C14 C9 C10 C11 1.9(2) . . . . ?
C15 O2 C12 C11 7.1(2) . . . . ?
C15 O2 C12 C13 -174.21(14) . . . . ?
C15 C16 C17 N4 58.8(2) . . . . ?
C17 N4 C18 C19 177.04(13) . . . . ?
C17 N4 C21 C20 -179.86(14) . . . . ?
C18 N4 C17 C16 50.79(18) . . . . ?
C18 N4 C21 C20 -54.84(17) . . . . ?
C19 O3 C20 C21 -59.3(2) . . . . ?
C20 O3 C19 C18 58.9(2) . . . . ?
C21 N4 C17 C16 173.18(14) . . . . ?
C21 N4 C18 C19 53.87(17) . . . . ?
C22 O1 C13 C12 178.64(16) . . . . ?
C22 O1 C13 C14 -1.3(3) . . . . ?
O4 N29 C23 C24 -21.7(3) . . . . ?
O4 N29 C23 C28 157.07(19) . . . . ?
O5 N29 C23 C24 158.97(18) . . . . ?
O5 N29 C23 C28 -22.3(3) . . . . ?
O8 N6 C27 C26 -12.9(3) . . . . ?
O8 N6 C27 C28 166.89(19) . . . . ?
O9 N6 C27 C26 167.0(2) . . . . ?
O9 N6 C27 C28 -13.2(3) . . . . ?
N6 C27 C28 C23 -179.60(16) . . . . ?
N29 C23 C24 C25 178.78(15) . . . . ?
N29 C23 C28 C27 -178.96(16) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C23 C24 C25 C29 -177.77(15) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C24 C25 C29 O6 -6.9(3) . . . . ?
C24 C25 C29 O7 170.46(17) . . . . ?
C25 C26 C27 N6 179.86(15) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C25 C29 O6 175.17(18) . . . . ?
C26 C25 C29 O7 -7.5(2) . . . . ?
C26 C27 C28 C23 0.2(3) . . . . ?
C28 C23 C24 C25 0.1(3) . . . . ?
C29 C25 C26 C27 177.72(15) . . . . ?
O12 N7 C32 C31 0.1(3) . . . . ?
O12 N7 C32 C33 179.6(2) . . . . ?
O13 N7 C32 C31 -179.68(19) . . . . ?
O13 N7 C32 C33 -0.2(3) . . . . ?
O14 N8 C34 C33 175.77(19) . . . . ?
O14 N8 C34 C35 -4.7(3) . . . . ?
O15 N8 C34 C33 -4.8(3) . . . . ?
O15 N8 C34 C35 174.74(18) . . . . ?
N7 C32 C33 C34 -179.42(16) . . . . ?
N8 C34 C35 C30 179.65(15) . . . . ?
C30 C31 C32 N7 179.43(16) . . . . ?
C30 C31 C32 C33 -0.1(3) . . . . ?
C31 C30 C35 C34 0.8(2) . . . . ?
C31 C30 C36 O10 170.59(18) . . . . ?
C31 C30 C36 O11 -11.5(3) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
C32 C33 C34 N8 179.90(15) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C33 C34 C35 C30 -0.9(3) . . . . ?
C35 C30 C31 C32 -0.4(3) . . . . ?
C35 C30 C36 O10 -11.0(3) . . . . ?
C35 C30 C36 O11 166.96(18) . . . . ?
C36 C30 C31 C32 178.02(16) . . . . ?
C36 C30 C35 C34 -177.57(16) . . . . ?

_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_samp7416
_database_code_depnum_ccdc_archive 'CCDC 2322082'
loop_
_audit_author_name
_audit_author_address
'Ningbo Gong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C22 H25 Cl F N4 O3, C22 H26 Cl F N4 O3, 3(C7 H5 O3), C7 H6 O3'
_chemical_formula_sum            'C72 H72 Cl2 F2 N8 O18'
_chemical_formula_weight         1446.28
_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 0.0181 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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.45160(10)
_cell_length_b                   18.00040(10)
_cell_length_c                   26.7026(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6946.27(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    63909
_cell_measurement_temperature    301.92(14)
_cell_measurement_theta_max      75.9190
_cell_measurement_theta_min      2.9240
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            130656
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.462
_diffrn_reflns_theta_min         2.961
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.92(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  29.00   0.50    0.16    --  -46.87  19.00  60.00  104
  2  ω    -40.00  26.00   0.50    0.16    --  -46.87  38.00 -60.00  132
  3  ω    -23.00  29.00   0.50    0.16    --  -46.87  19.00 -90.00  104
  4  ω    -23.00  29.00   0.50    0.16    --  -46.87  19.00-180.00  104
  5  ω     74.00 100.00   0.50    0.62    --  104.56 -95.00-120.00   52
  6  ω     35.00 115.00   0.50    0.16    --   46.87-157.00-146.00  160
  7  ω     35.00 134.00   0.50    0.62    --  104.56-157.00-146.00  198
  8  ω     37.00 103.00   0.50    0.62    --  104.56-125.00-150.00  132
  9  ω     52.00 110.00   0.50    0.62    --  104.56-125.00-120.00  116
 10  ω     16.00  90.00   0.50    0.16    --   46.87-120.00   8.00  148
 11  ω     35.00 111.00   0.50    0.62    --  104.56-125.00 -90.00  152
 12  ω     37.00 111.00   0.50    0.62    --  104.56-125.00 -30.00  148
 13  ω     35.00 110.00   0.50    0.62    --  104.56-120.00   8.00  150
 14  ω     48.00 102.00   0.50    0.62    --  104.56 -95.00  30.00  108
 15  ω     34.00  63.00   0.50    0.62    --  104.56 -77.00   0.00   58
 16  ω     33.00  70.00   0.50    0.62    --  104.56 -61.00  30.00   74
 17  ω     39.00  73.00   0.50    0.62    --  104.56 -61.00  60.00   68
 18  ω     73.00  98.00   0.50    0.62    --  104.56 -77.00   0.00   50
 19  ω     32.00  57.00   0.50    0.62    --  104.56 -61.00 -30.00   50
 20  ω     33.00  71.00   0.50    0.62    --  104.56 -61.00-180.00   76
 21  ω     95.00 176.00   0.50    0.62    --  104.56  30.00 -90.00  162
 22  ω     92.00 169.00   0.50    0.62    --  104.56  45.00-180.00  154
 23  ω     35.00 120.00   0.50    0.16    --   46.87  38.00-150.00  170
 24  ω     24.00 118.00   0.50    0.16    --   46.87  77.00  90.00  188
 25  ω     89.00 175.00   0.50    0.62    --  104.56  61.00 120.00  172
 26  ω     83.00 174.00   0.50    0.62    --  104.56 120.00  92.00  182
 27  ω     82.00 108.00   0.50    0.62    --  104.56 125.00  30.00   52
 28  ω    117.00 151.00   0.50    0.62    --  104.56 125.00  30.00   68
 29  ω     58.00 160.00   0.50    0.62    --  104.56 157.00-112.00  204
 30  ω     58.00 120.00   0.50    0.16    --   46.87 157.00-112.00  124
 31  ω   -114.00 -29.00   0.50    0.16    --  -46.87 157.00-112.00  170
 32  ω   -133.00 -30.00   0.50    0.62    -- -103.00 157.00-112.00  206
 33  ω    -90.00  -9.00   0.50    0.16    --  -46.87 120.00  92.00  162
 34  ω   -109.00 -33.00   0.50    0.62    -- -103.00 120.00  92.00  152
 35  ω   -102.00 -45.00   0.50    0.62    -- -103.00  77.00  90.00  114
 36  ω    -67.00 -41.00   0.50    0.62    -- -103.00  61.00 -60.00   52
 37  ω    -74.00 -34.00   0.50    0.62    -- -103.00  77.00-120.00   80
 38  ω   -155.00 -91.00   0.50    0.62    -- -103.00 -15.00  60.00  128
 39  ω   -111.00 -86.00   0.50    0.62    -- -103.00 -61.00  90.00   50
 40  ω   -174.00 -90.00   0.50    0.62    -- -103.00 -45.00  30.00  168
 41  ω   -171.00-133.00   0.50    0.62    -- -103.00 -61.00  90.00   76
 42  ω   -173.00 -77.00   0.50    0.62    -- -103.00-120.00   8.00  192
 43  ω   -119.00 -51.00   0.50    0.16    --  -46.87-157.00-146.00  136
 44  ω   -160.00 -51.00   0.50    0.62    -- -103.00-157.00-146.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151971000
_diffrn_orient_matrix_UB_12      -0.0653107000
_diffrn_orient_matrix_UB_13      -0.0363854000
_diffrn_orient_matrix_UB_21      0.0053587000
_diffrn_orient_matrix_UB_22      0.0549299000
_diffrn_orient_matrix_UB_23      -0.0441502000
_diffrn_orient_matrix_UB_31      0.1053480000
_diffrn_orient_matrix_UB_32      0.0066497000
_diffrn_orient_matrix_UB_33      0.0074925000
_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         0.810
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                12776
_reflns_number_total             14320
_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 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_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         0.374
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 5067 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_coef       0.00064(10)
_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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1129
_refine_ls_number_reflns         14320
_refine_ls_number_restraints     286
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.021
_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)+(0.0905P)²+1.1201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 Cl1C-C2A \\sim Cl1A-C4C
 with sigma of 0.02
 C6A-C5A \\sim C6A-C1C
 with sigma of 0.02
 C6A-C1A \\sim C6A-C5C
 with sigma of 0.02
 F1C-C3A \\sim F1A-C3C
 with sigma of 0.02
 C5A-C4A \\sim C1C-C2C
 with sigma of 0.02
 C1A-C2A \\sim C5C-C4C
 with sigma of 0.02
 C4A-C3A \\sim C2C-C3C
 with sigma of 0.02
 C2A-C3A \\sim C4C-C3C
 with sigma of 0.02
 Cl1C-C1A \\sim Cl1A-C5C
 with sigma of 0.04
 Cl1C-C3A \\sim Cl1A-C3C
 with sigma of 0.04
 C6A-C4A \\sim C6A-C2C
 with sigma of 0.04
 C6A-C2A \\sim C6A-C4C
 with sigma of 0.04
 F1C-C4A \\sim F1A-C2C
 with sigma of 0.04
 F1C-C2A \\sim F1A-C4C
 with sigma of 0.04
 C5A-C3A \\sim C1C-C3C
 with sigma of 0.04
 C1A-C3A \\sim C5C-C3C
 with sigma of 0.04
 C4A-C2A \\sim C2C-C4C
 with sigma of 0.04
 O4B-C29B \\sim O4F-C29F
 with sigma of 0.02
 C23B-C28B \\sim C23F-C28F
 with sigma of 0.02
 C23B-C29B \\sim C23F-C29F
 with sigma of 0.02
 C23B-C24B \\sim C23F-C24F
 with sigma of 0.02
 C28B-C27B \\sim C28F-C27F
 with sigma of 0.02
 C29B-O5B \\sim C29F-O5F
 with sigma of 0.02
 C25B-C24B \\sim C25F-C24F
 with sigma of 0.02
 C25B-C26B \\sim C25F-C26F
 with sigma of 0.02
 O6B-C24B \\sim O6F-C24F
 with sigma of 0.02
 C27B-C26B \\sim C27F-C26F
 with sigma of 0.02
 O4B-C23B \\sim O4F-C23F
 with sigma of 0.04
 O4B-O5B \\sim O4F-O5F
 with sigma of 0.04
 C23B-C25B \\sim C23F-C25F
 with sigma of 0.04
 C23B-O6B \\sim C23F-O6F
 with sigma of 0.04
 C23B-O5B \\sim C23F-O5F
 with sigma of 0.04
 C23B-C27B \\sim C23F-C27F
 with sigma of 0.04
 C28B-C29B \\sim C28F-C29F
 with sigma of 0.04
 C28B-C24B \\sim C28F-C24F
 with sigma of 0.04
 C28B-C26B \\sim C28F-C26F
 with sigma of 0.04
 C29B-C24B \\sim C29F-C24F
 with sigma of 0.04
 C25B-O6B \\sim C25F-O6F
 with sigma of 0.04
 C25B-C27B \\sim C25F-C27F
 with sigma of 0.04
 C24B-C26B \\sim C24F-C26F
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 O4F, O5F, O6F, C23F, C24F, C25F, C26F, C27F, C28F, C29F
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O4B, O5B, O6B, C23B, C24B, C25B, C26B, C27B, C28B, C29B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N2A, N3A, C7A, C8A, C9A, C10A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C6A, C1A, C2A, C3A, C4A, C5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C6A, C1C, C2C, C3C, C4C, C5C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(Cl1A)=Sof(F1A)=Sof(C1C)=Sof(H1C)=Sof(C2C)=Sof(H2C)=Sof(C3C)=Sof(C4C)=
 Sof(C5C)=Sof(H5C)=1-FVAR(1)
 Sof(Cl1C)=Sof(F1C)=Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(H4AA)=
 Sof(C5A)=Sof(H5A)=FVAR(1)
 Sof(O4F)=Sof(O5F)=Sof(O6F)=Sof(H6F)=Sof(C23F)=Sof(C24F)=Sof(C25F)=Sof(H25F)=
 Sof(C26F)=Sof(H26F)=Sof(C27F)=Sof(H27F)=Sof(C28F)=Sof(H28F)=Sof(C29F)=1-FVAR(2)
 Sof(O4B)=Sof(O5B)=Sof(O6B)=Sof(H6B)=Sof(C23B)=Sof(C24B)=Sof(C25B)=Sof(H25B)=
 Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=Sof(C28B)=Sof(H28B)=Sof(C29B)=FVAR(2)
 Sof(H4BA)=Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C18B)=
 Sof(H18C)=Sof(H18D)=Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20C)=Sof(H20C)=
 Sof(H20D)=Sof(C21C)=Sof(H21C)=Sof(H21D)=1-FVAR(3)
 Sof(H4B)=Sof(H16A)=Sof(H16B)=Sof(C17C)=Sof(H17A)=Sof(H17B)=Sof(C18C)=
 Sof(H18A)=Sof(H18B)=Sof(C19C)=Sof(H19A)=Sof(H19B)=Sof(C20B)=Sof(H20A)=
 Sof(H20B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 N4B(H4B), N4B(H4BA), N4A(H4A)
5.b Secondary CH2 refined with riding coordinates:
 C15B(H15A,H15B), C16B(H16A,H16B), C16B(H16C,H16D), C17C(H17A,H17B), C18C(H18A,
 H18B), C19C(H19A,H19B), C20B(H20A,H20B), C21B(H21A,H21B), C17B(H17C,H17D),
 C18B(H18C,H18D), C19B(H19C,H19D), C20C(H20C,H20D), C21C(H21C,H21D), C15A(H15C,
 H15D), C16A(H16E,H16F), C17A(H17E,H17F), C18A(H18E,H18F), C19A(H19E,H19F),
 C20A(H20E,H20F), C21A(H21E,H21F)
5.c Aromatic/amide H refined with riding coordinates:
 N1B(H1B), N3B(H3B), C1B(H1BA), C2B(H2B), C5B(H5B), C8B(H8B), C11B(H11B),
 C14B(H14B), N1A(H1A), C8A(H8A), C11A(H11A), C14A(H14A), C1A(H1AA), C4A(H4AA),
 C5A(H5A), C1C(H1C), C2C(H2C), C5C(H5C), C25A(H25A), C26A(H26A), C27A(H27A),
 C28A(H28A), C25C(H25C), C26C(H26C), C27C(H27C), C28C(H28C), C25D(H25D),
 C26D(H26D), C27D(H27D), C28D(H28D), C25B(H25B), C26B(H26B), C27B(H27B),
 C28B(H28B), C25F(H25F), C26F(H26F), C27F(H27F), C28F(H28F)
5.d Idealised Me refined as rotating group:
 C22B(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
5.e Idealised tetrahedral OH refined as rotating group:
 O6A(H6A), O6C(H6C), O5D(H5D), O6D(H6D), O6B(H6B), O6F(H6F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1B Cl 0.45320(12) 0.09702(10) 0.69962(4) 0.1119(5) Uani 1 1 d . . . . .
F1B F 0.3915(3) -0.04373(18) 0.65668(13) 0.1214(12) Uani 1 1 d . . . . .
O1B O 0.4432(2) 0.44294(13) 0.35498(9) 0.0675(6) Uani 1 1 d . . . . .
O2B O 0.40213(17) 0.45729(11) 0.44774(8) 0.0568(5) Uani 1 1 d . . . . .
O3B O 0.2848(3) 0.80000(18) 0.56564(17) 0.1010(10) Uani 1 1 d . . . . .
N1B N 0.41687(19) 0.18586(15) 0.52072(10) 0.0560(6) Uani 1 1 d . . . . .
H1B H 0.402604 0.228121 0.533610 0.067 Uiso 1 1 calc R U . . .
N2B N 0.4637(2) 0.12087(15) 0.45110(11) 0.0649(7) Uani 1 1 d . . . . .
N3B N 0.4842(2) 0.17942(15) 0.37413(10) 0.0609(7) Uani 1 1 d . . . . .
H3B H 0.497943 0.174724 0.342946 0.073 Uiso 1 1 calc R U . . .
N4B N 0.2668(2) 0.64292(17) 0.55919(11) 0.0675(8) Uani 1 1 d . . . . .
H4B H 0.210981 0.642726 0.580021 0.081 Uiso 0.626(13) 1 calc R U P A 1
H4BA H 0.200320 0.632951 0.556595 0.081 Uiso 0.374(13) 1 calc R U P A 2
C1B C 0.3841(3) 0.05323(19) 0.53884(15) 0.0643(8) Uani 1 1 d . . . . .
H1BA H 0.369080 0.043787 0.505574 0.077 Uiso 1 1 calc R U . . .
C2B C 0.3780(3) -0.0028(2) 0.57409(18) 0.0773(11) Uani 1 1 d . . . . .
H2B H 0.359174 -0.050111 0.564513 0.093 Uiso 1 1 calc R U . . .
C3B C 0.3993(3) 0.0110(2) 0.62217(17) 0.0808(12) Uani 1 1 d . . . . .
C4B C 0.4276(3) 0.0801(3) 0.63782(15) 0.0777(11) Uani 1 1 d . . . . .
C5B C 0.4352(3) 0.1371(2) 0.60283(13) 0.0662(8) Uani 1 1 d . . . . .
H5B H 0.455339 0.183961 0.612737 0.079 Uiso 1 1 calc R U . . .
C6B C 0.4128(2) 0.12385(18) 0.55334(12) 0.0571(7) Uani 1 1 d . . . . .
C7B C 0.4403(2) 0.18643(16) 0.47220(11) 0.0511(6) Uani 1 1 d . . . . .
C8B C 0.4840(3) 0.12067(19) 0.40326(14) 0.0681(9) Uani 1 1 d . . . . .
H8B H 0.499532 0.075336 0.388814 0.082 Uiso 1 1 calc R U . . .
C9B C 0.4627(2) 0.24854(16) 0.39301(11) 0.0514(6) Uani 1 1 d . . . . .
C10B C 0.44062(19) 0.25418(16) 0.44394(11) 0.0483(6) Uani 1 1 d . . . . .
C11B C 0.4202(2) 0.32546(16) 0.46348(11) 0.0478(6) Uani 1 1 d . . . . .
H11B H 0.406052 0.330713 0.497265 0.057 Uiso 1 1 calc R U . . .
C12B C 0.4212(2) 0.38661(16) 0.43315(11) 0.0485(6) Uani 1 1 d . . . . .
C13B C 0.4442(2) 0.37943(17) 0.38133(11) 0.0522(6) Uani 1 1 d . . . . .
C14B C 0.4638(2) 0.31076(18) 0.36193(11) 0.0557(7) Uani 1 1 d . . . . .
H14B H 0.477818 0.305663 0.328109 0.067 Uiso 1 1 calc R U . . .
C15B C 0.3719(2) 0.46891(17) 0.49822(11) 0.0512(6) Uani 1 1 d . . . . .
H15A H 0.420856 0.456491 0.521597 0.061 Uiso 1 1 calc R U . . .
H15B H 0.318460 0.438131 0.505534 0.061 Uiso 1 1 calc R U . . .
C16B C 0.3470(2) 0.55019(17) 0.50242(12) 0.0573(7) Uani 1 1 d . . . . .
H16A H 0.317094 0.566664 0.471857 0.069 Uiso 0.626(13) 1 calc R U P A 1
H16B H 0.402635 0.579508 0.507191 0.069 Uiso 0.626(13) 1 calc R U P A 1
H16C H 0.396162 0.579661 0.487682 0.069 Uiso 0.374(13) 1 calc R U P A 2
H16D H 0.290985 0.559411 0.483403 0.069 Uiso 0.374(13) 1 calc R U P A 2
C22B C 0.4663(4) 0.4389(2) 0.30271(14) 0.0814(11) Uani 1 1 d . . . . .
H22A H 0.421939 0.408291 0.285692 0.122 Uiso 1 1 calc R U . . .
H22B H 0.526935 0.417845 0.298966 0.122 Uiso 1 1 calc R U . . .
H22C H 0.465496 0.487939 0.288554 0.122 Uiso 1 1 calc R U . . .
C17C C 0.2813(6) 0.5612(3) 0.5472(2) 0.0565(16) Uani 0.626(13) 1 d . . P A 1
H17A H 0.222048 0.538471 0.539656 0.068 Uiso 0.626(13) 1 calc R U P A 1
H17B H 0.306812 0.536320 0.576326 0.068 Uiso 0.626(13) 1 calc R U P A 1
C18C C 0.3330(6) 0.6754(5) 0.5902(4) 0.0659(19) Uani 0.626(13) 1 d . . P A 1
H18A H 0.391962 0.677034 0.572870 0.079 Uiso 0.626(13) 1 calc R U P A 1
H18B H 0.340571 0.645423 0.620077 0.079 Uiso 0.626(13) 1 calc R U P A 1
C19C C 0.3049(8) 0.7530(4) 0.6048(3) 0.078(2) Uani 0.626(13) 1 d . . P A 1
H19A H 0.250907 0.749866 0.626312 0.094 Uiso 0.626(13) 1 calc R U P A 1
H19B H 0.354518 0.774837 0.624384 0.094 Uiso 0.626(13) 1 calc R U P A 1
C20B C 0.2125(10) 0.7653(12) 0.5327(8) 0.085(4) Uani 0.626(13) 1 d . . P A 1
H20A H 0.202667 0.796702 0.503692 0.102 Uiso 0.626(13) 1 calc R U P A 1
H20B H 0.154597 0.762520 0.551029 0.102 Uiso 0.626(13) 1 calc R U P A 1
C21B C 0.2394(7) 0.6883(3) 0.5155(2) 0.068(2) Uani 0.626(13) 1 d . . P A 1
H21A H 0.187594 0.665151 0.498505 0.082 Uiso 0.626(13) 1 calc R U P A 1
H21B H 0.290575 0.691549 0.492067 0.082 Uiso 0.626(13) 1 calc R U P A 1
C17B C 0.3328(12) 0.5740(7) 0.5535(4) 0.066(3) Uani 0.374(13) 1 d . . P A 2
H17C H 0.392380 0.586174 0.568056 0.079 Uiso 0.374(13) 1 calc R U P A 2
H17D H 0.307195 0.532828 0.572407 0.079 Uiso 0.374(13) 1 calc R U P A 2
C18B C 0.2998(12) 0.6820(8) 0.6078(5) 0.066(3) Uani 0.374(13) 1 d . . P A 2
H18C H 0.286922 0.650593 0.636510 0.079 Uiso 0.374(13) 1 calc R U P A 2
H18D H 0.366033 0.690333 0.606292 0.079 Uiso 0.374(13) 1 calc R U P A 2
C19B C 0.2501(15) 0.7555(7) 0.6136(5) 0.079(4) Uani 0.374(13) 1 d . . P A 2
H19C H 0.267974 0.780349 0.644374 0.095 Uiso 0.374(13) 1 calc R U P A 2
H19D H 0.183489 0.748952 0.613226 0.095 Uiso 0.374(13) 1 calc R U P A 2
C20C C 0.251(2) 0.7743(15) 0.5296(9) 0.092(8) Uani 0.374(13) 1 d . . P A 2
H20C H 0.253196 0.808992 0.501829 0.111 Uiso 0.374(13) 1 calc R U P A 2
H20D H 0.186750 0.760946 0.535797 0.111 Uiso 0.374(13) 1 calc R U P A 2
C21C C 0.3102(13) 0.7040(6) 0.5185(4) 0.078(4) Uani 0.374(13) 1 d . . P A 2
H21C H 0.375373 0.713114 0.524674 0.093 Uiso 0.374(13) 1 calc R U P A 2
H21D H 0.302157 0.687289 0.484212 0.093 Uiso 0.374(13) 1 calc R U P A 2
O1A O 0.6609(2) 0.50704(15) 0.35817(12) 0.0883(9) Uani 1 1 d . . . . .
O2A O 0.6975(2) 0.37273(14) 0.33895(9) 0.0718(7) Uani 1 1 d . . . . .
O3A O 0.6688(3) 0.16270(16) 0.09811(10) 0.0956(10) Uani 1 1 d . . . . .
N1A N 0.6793(2) 0.2332(2) 0.51064(10) 0.0666(7) Uani 1 1 d . . . . .
H1A H 0.697852 0.220109 0.481350 0.080 Uiso 1 1 calc R U . . .
N2A N 0.6306(3) 0.3279(3) 0.56196(13) 0.0856(9) Uani 1 1 d . . . . .
N3A N 0.6130(2) 0.4503(2) 0.53206(14) 0.0807(9) Uani 1 1 d . . . . .
N4A N 0.67628(19) 0.20535(14) 0.20066(9) 0.0541(6) Uani 1 1 d . . . . .
H4A H 0.610284 0.213457 0.207080 0.065 Uiso 1 1 calc R U . . .
C6A C 0.6748(2) 0.1766(3) 0.54715(14) 0.0757(9) Uani 1 1 d D . . . .
C7A C 0.6579(2) 0.3055(2) 0.51650(12) 0.0630(7) Uani 1 1 d . . . . .
C8A C 0.6096(3) 0.4005(3) 0.56669(18) 0.0884(11) Uani 1 1 d . . . . .
H8A H 0.590622 0.416257 0.598226 0.106 Uiso 1 1 calc R U . . .
C9A C 0.6380(2) 0.4304(2) 0.48441(14) 0.0645(8) Uani 1 1 d . . . . .
C10A C 0.6613(2) 0.3551(2) 0.47515(12) 0.0575(7) Uani 1 1 d . . . . .
C11A C 0.6841(2) 0.33487(19) 0.42554(11) 0.0552(7) Uani 1 1 d . . . . .
H11A H 0.701326 0.286226 0.418371 0.066 Uiso 1 1 calc R U . . .
C12A C 0.6811(2) 0.38636(18) 0.38817(13) 0.0597(7) Uani 1 1 d . . . . .
C13A C 0.6585(3) 0.4618(2) 0.39868(15) 0.0664(9) Uani 1 1 d . . . . .
C14A C 0.6374(3) 0.4827(2) 0.44633(17) 0.0696(9) Uani 1 1 d . . . . .
H14A H 0.622610 0.531915 0.453289 0.083 Uiso 1 1 calc R U . . .
C15A C 0.7179(3) 0.29815(19) 0.32442(13) 0.0646(8) Uani 1 1 d . . . . .
H15C H 0.674544 0.263853 0.339739 0.078 Uiso 1 1 calc R U . . .
H15D H 0.780089 0.284621 0.334600 0.078 Uiso 1 1 calc R U . . .
C16A C 0.7092(3) 0.2962(2) 0.26847(13) 0.0683(9) Uani 1 1 d . . . . .
H16E H 0.753453 0.330343 0.253784 0.082 Uiso 1 1 calc R U . . .
H16F H 0.647617 0.312241 0.258894 0.082 Uiso 1 1 calc R U . . .
C17A C 0.7265(3) 0.2186(2) 0.24843(13) 0.0656(8) Uani 1 1 d . . . . .
H17E H 0.792307 0.211838 0.242999 0.079 Uiso 1 1 calc R U . . .
H17F H 0.706574 0.182417 0.273096 0.079 Uiso 1 1 calc R U . . .
C18A C 0.6877(3) 0.12672(19) 0.18402(15) 0.0728(10) Uani 1 1 d . . . . .
H18E H 0.663797 0.093506 0.209535 0.087 Uiso 1 1 calc R U . . .
H18F H 0.752892 0.115884 0.179392 0.087 Uiso 1 1 calc R U . . .
C19A C 0.6371(4) 0.1142(2) 0.13599(16) 0.0905(13) Uani 1 1 d . . . . .
H19E H 0.645857 0.063204 0.125286 0.109 Uiso 1 1 calc R U . . .
H19F H 0.571419 0.122081 0.141296 0.109 Uiso 1 1 calc R U . . .
C20A C 0.6525(4) 0.2377(2) 0.11243(15) 0.0883(14) Uani 1 1 d . . . . .
H20E H 0.586760 0.245170 0.117714 0.106 Uiso 1 1 calc R U . . .
H20F H 0.672240 0.270571 0.085720 0.106 Uiso 1 1 calc R U . . .
C21A C 0.7042(3) 0.25640(19) 0.15962(13) 0.0662(9) Uani 1 1 d . . . . .
H21E H 0.770204 0.252071 0.153782 0.079 Uiso 1 1 calc R U . . .
H21F H 0.690999 0.307281 0.169222 0.079 Uiso 1 1 calc R U . . .
C22A C 0.6461(6) 0.5841(3) 0.3660(3) 0.124(2) Uani 1 1 d . . . . .
H22D H 0.654312 0.610259 0.335006 0.187 Uiso 1 1 calc R U . . .
H22E H 0.689592 0.602262 0.390261 0.187 Uiso 1 1 calc R U . . .
H22F H 0.584260 0.591899 0.378089 0.187 Uiso 1 1 calc R U . . .
Cl1C Cl 0.7341(2) 0.1095(3) 0.68316(11) 0.1087(15) Uani 0.393(4) 1 d D . P B 1
F1C F 0.6558(8) -0.0176(6) 0.6351(5) 0.098(3) Uani 0.393(4) 1 d D . P B 1
C1A C 0.7029(9) 0.1669(7) 0.5940(5) 0.065(2) Uani 0.393(4) 1 d D . P B 1
H1AA H 0.730461 0.208279 0.608633 0.078 Uiso 0.393(4) 1 calc R U P B 1
C2A C 0.6977(9) 0.1054(9) 0.6244(5) 0.066(3) Uani 0.393(4) 1 d D . P B 1
C3A C 0.6610(8) 0.0418(7) 0.6029(5) 0.066(3) Uani 0.393(4) 1 d D . P B 1
C4A C 0.6344(12) 0.0402(10) 0.5530(5) 0.073(3) Uani 0.393(4) 1 d D . P B 1
H4AA H 0.615709 -0.004297 0.538388 0.088 Uiso 0.393(4) 1 calc R U P B 1
C5A C 0.6357(19) 0.1057(11) 0.5245(7) 0.077(3) Uani 0.393(4) 1 d D . P B 1
H5A H 0.612744 0.105741 0.491946 0.092 Uiso 0.393(4) 1 calc R U P B 1
Cl1A Cl 0.6180(2) -0.03046(11) 0.55023(16) 0.1519(17) Uani 0.607(4) 1 d D . P B
2
F1A F 0.6776(11) 0.0143(7) 0.6517(4) 0.196(7) Uani 0.607(4) 1 d D . P B 2
C1C C 0.7013(9) 0.1992(6) 0.5978(4) 0.090(2) Uani 0.607(4) 1 d D . P B 2
H1C H 0.716107 0.247934 0.606236 0.108 Uiso 0.607(4) 1 calc R U P B 2
C2C C 0.7021(10) 0.1407(7) 0.6324(4) 0.113(4) Uani 0.607(4) 1 d D . P B 2
H2C H 0.719578 0.149777 0.665324 0.136 Uiso 0.607(4) 1 calc R U P B 2
C3C C 0.6775(11) 0.0705(7) 0.6183(4) 0.109(4) Uani 0.607(4) 1 d D . P B 2
C4C C 0.6509(9) 0.0527(7) 0.5704(5) 0.096(3) Uani 0.607(4) 1 d D . P B 2
C5C C 0.6527(11) 0.1088(7) 0.5351(5) 0.076(2) Uani 0.607(4) 1 d D . P B 2
H5C H 0.637809 0.097891 0.502063 0.091 Uiso 0.607(4) 1 calc R U P B 2
O4A O 0.5141(2) 0.16696(18) 0.27465(10) 0.0779(7) Uani 1 1 d . . . . .
O5A O 0.4905(2) 0.2419(2) 0.21124(11) 0.0906(9) Uani 1 1 d . . . . .
O6A O 0.3326(3) 0.3133(3) 0.20778(17) 0.1137(12) Uani 1 1 d . . . . .
H6A H 0.388829 0.309552 0.204689 0.171 Uiso 1 1 calc R U . . .
C23A C 0.3598(3) 0.2033(2) 0.25694(12) 0.0669(9) Uani 1 1 d . . . . .
C24A C 0.3007(3) 0.2572(3) 0.23667(15) 0.0826(11) Uani 1 1 d . . . . .
C25A C 0.2067(4) 0.2562(5) 0.2467(2) 0.117(2) Uani 1 1 d . . . . .
H25A H 0.168485 0.292494 0.233031 0.140 Uiso 1 1 calc R U . . .
C26A C 0.1704(4) 0.2031(6) 0.2760(2) 0.132(3) Uani 1 1 d . . . . .
H26A H 0.107103 0.202532 0.282308 0.158 Uiso 1 1 calc R U . . .
C27A C 0.2252(5) 0.1503(5) 0.2965(2) 0.122(2) Uani 1 1 d . . . . .
H27A H 0.199564 0.114240 0.317229 0.146 Uiso 1 1 calc R U . . .
C28A C 0.3189(4) 0.1498(3) 0.28697(17) 0.0922(13) Uani 1 1 d . . . . .
H28A H 0.355447 0.112672 0.300963 0.111 Uiso 1 1 calc R U . . .
C29A C 0.4607(3) 0.2033(2) 0.24715(12) 0.0656(9) Uani 1 1 d . . . . .
O4C O 0.7260(2) 0.15580(17) 0.42246(10) 0.0834(8) Uani 1 1 d . . . . .
O5C O 0.8717(2) 0.19246(15) 0.41663(10) 0.0804(8) Uani 1 1 d . . . . .
O6C O 0.9698(3) 0.1516(3) 0.34261(15) 0.1071(11) Uani 1 1 d . . . . .
H6C H 0.956988 0.175014 0.368017 0.161 Uiso 1 1 calc R U . . .
C23C C 0.8174(3) 0.10452(18) 0.35785(11) 0.0592(8) Uani 1 1 d . . . . .
C24C C 0.9002(3) 0.1057(2) 0.33144(14) 0.0735(10) Uani 1 1 d . . . . .
C25C C 0.9128(4) 0.0586(3) 0.29044(18) 0.1004(16) Uani 1 1 d . . . . .
H25C H 0.967314 0.060750 0.272015 0.120 Uiso 1 1 calc R U . . .
C26C C 0.8455(5) 0.0097(3) 0.2775(2) 0.1083(19) Uani 1 1 d . . . . .
H26C H 0.855206 -0.022593 0.250756 0.130 Uiso 1 1 calc R U . . .
C27C C 0.7633(5) 0.0071(3) 0.3032(2) 0.0995(16) Uani 1 1 d . . . . .
H27C H 0.717401 -0.026382 0.293863 0.119 Uiso 1 1 calc R U . . .
C28C C 0.7492(3) 0.0552(2) 0.34346(15) 0.0758(10) Uani 1 1 d . . . . .
H28C H 0.693358 0.054019 0.360766 0.091 Uiso 1 1 calc R U . . .
C29C C 0.8030(3) 0.15433(18) 0.40203(11) 0.0625(8) Uani 1 1 d . . . . .
O4D O 0.5508(4) 0.5476(2) 0.6172(2) 0.1322(16) Uani 1 1 d . . . . .
O5D O 0.5770(3) 0.5981(3) 0.54471(15) 0.1131(13) Uani 1 1 d . . . . .
H5D H 0.576717 0.554281 0.536306 0.170 Uiso 1 1 calc R U . . .
O6D O 0.5268(5) 0.6267(4) 0.69330(17) 0.1476(18) Uani 1 1 d . . . . .
H6D H 0.537216 0.588379 0.677722 0.221 Uiso 1 1 calc R U . . .
C23D C 0.5562(2) 0.6773(2) 0.61307(17) 0.0715(9) Uani 1 1 d . . . . .
C24D C 0.5389(3) 0.6836(3) 0.6641(2) 0.0891(13) Uani 1 1 d . . . . .
C25D C 0.5322(4) 0.7542(5) 0.6859(3) 0.131(3) Uani 1 1 d . . . . .
H25D H 0.521552 0.758807 0.720065 0.157 Uiso 1 1 calc R U . . .
C26D C 0.5411(6) 0.8159(5) 0.6571(5) 0.154(4) Uani 1 1 d . . . . .
H26D H 0.537501 0.862799 0.671600 0.185 Uiso 1 1 calc R U . . .
C27D C 0.5548(6) 0.8092(4) 0.6087(5) 0.158(4) Uani 1 1 d . . . . .
H27D H 0.559175 0.851988 0.589342 0.189 Uiso 1 1 calc R U . . .
C28D C 0.5630(4) 0.7419(3) 0.5857(3) 0.1066(17) Uani 1 1 d . . . . .
H28D H 0.573174 0.739640 0.551310 0.128 Uiso 1 1 calc R U . . .
C29D C 0.5617(3) 0.6028(3) 0.5897(2) 0.0850(13) Uani 1 1 d . . . . .
O4B O 0.1114(4) 0.6186(4) 0.6125(2) 0.0904(17) Uani 0.591(7) 1 d D . P C 1
O5B O 0.0351(5) 0.6252(5) 0.5411(3) 0.120(2) Uani 0.591(7) 1 d D . P C 1
O6B O -0.1328(4) 0.5915(4) 0.5383(2) 0.1009(18) Uani 0.591(7) 1 d D . P C 1
H6B H -0.086149 0.614435 0.530040 0.151 Uiso 0.591(7) 1 calc R U P C 1
C23B C -0.0460(5) 0.5841(6) 0.6123(4) 0.0718(14) Uani 0.591(7) 1 d D . P C 1
C24B C -0.1276(5) 0.5743(4) 0.5861(3) 0.0729(12) Uani 0.591(7) 1 d D . P C 1
C25B C -0.2074(8) 0.5516(10) 0.6092(4) 0.094(3) Uani 0.591(7) 1 d D . P C 1
H25B H -0.261878 0.546579 0.590948 0.113 Uiso 0.591(7) 1 calc R U P C 1
C26B C -0.2064(6) 0.5360(5) 0.6605(4) 0.0887(18) Uani 0.591(7) 1 d D . P C 1
H26B H -0.260548 0.521159 0.676419 0.106 Uiso 0.591(7) 1 calc R U P C 1
C27B C -0.1228(5) 0.5427(5) 0.6885(4) 0.0840(16) Uani 0.591(7) 1 d D . P C 1
H27B H -0.121846 0.531170 0.722465 0.101 Uiso 0.591(7) 1 calc R U P C 1
C28B C -0.0426(5) 0.5666(4) 0.6644(3) 0.0745(14) Uani 0.591(7) 1 d D . P C 1
H28B H 0.012482 0.571194 0.682128 0.089 Uiso 0.591(7) 1 calc R U P C 1
C29B C 0.0395(5) 0.6102(5) 0.5862(4) 0.0791(16) Uani 0.591(7) 1 d D . P C 1
O4F O 0.0895(11) 0.6259(11) 0.5421(7) 0.173(5) Uani 0.409(7) 1 d D . P C 2
O5F O 0.1261(8) 0.5778(9) 0.6123(6) 0.143(4) Uani 0.409(7) 1 d D . P C 2
O6F O 0.0139(7) 0.5550(8) 0.6766(6) 0.140(3) Uani 0.409(7) 1 d D . P C 2
H6F H 0.051594 0.588117 0.671397 0.210 Uiso 0.409(7) 1 calc R U P C 2
C23F C -0.0307(10) 0.5828(9) 0.5959(7) 0.109(2) Uani 0.409(7) 1 d D . P C 2
C24F C -0.0568(9) 0.5608(7) 0.6434(8) 0.109(2) Uani 0.409(7) 1 d D . P C 2
C25F C -0.1489(10) 0.5437(6) 0.6576(7) 0.112(2) Uani 0.409(7) 1 d D . P C 2
H25F H -0.164982 0.529816 0.689969 0.135 Uiso 0.409(7) 1 calc R U P C 2
C26F C -0.2116(14) 0.5493(10) 0.6199(8) 0.111(3) Uani 0.409(7) 1 d D . P C 2
H26F H -0.272457 0.535948 0.626680 0.134 Uiso 0.409(7) 1 calc R U P C 2
C27F C -0.1898(10) 0.5745(9) 0.5701(8) 0.132(3) Uani 0.409(7) 1 d D . P C 2
H27F H -0.236442 0.580577 0.546442 0.158 Uiso 0.409(7) 1 calc R U P C 2
C28F C -0.0954(11) 0.5901(10) 0.5574(8) 0.130(4) Uani 0.409(7) 1 d D . P C 2
H28F H -0.078144 0.604336 0.525288 0.156 Uiso 0.409(7) 1 calc R U P C 2
C29F C 0.0688(11) 0.5978(13) 0.5837(9) 0.131(4) Uani 0.409(7) 1 d D . P C 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
Cl1B C4B 1.718(4) . ?
F1B C3B 1.354(5) . ?
O1B C13B 1.342(4) . ?
O1B C22B 1.437(4) . ?
O2B C12B 1.359(3) . ?
O2B C15B 1.432(4) . ?
O3B C19C 1.376(9) . ?
O3B C20B 1.502(17) . ?
O3B C19B 1.593(15) . ?
O3B C20C 1.18(3) . ?
N1B H1B 0.8600 . ?
N1B C6B 1.417(4) . ?
N1B C7B 1.339(4) . ?
N2B C7B 1.351(4) . ?
N2B C8B 1.311(5) . ?
N3B H3B 0.8600 . ?
N3B C8B 1.313(5) . ?
N3B C9B 1.378(4) . ?
N4B H4B 0.9800 . ?
N4B H4BA 0.9800 . ?
N4B C17C 1.521(6) . ?
N4B C18C 1.393(8) . ?
N4B C21B 1.479(6) . ?
N4B C17B 1.573(11) . ?
N4B C18B 1.552(12) . ?
N4B C21C 1.669(13) . ?
C1B H1BA 0.9300 . ?
C1B C2B 1.382(5) . ?
C1B C6B 1.392(5) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.343(7) . ?
C3B C4B 1.374(7) . ?
C4B C5B 1.392(6) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.381(5) . ?
C7B C10B 1.434(4) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.401(4) . ?
C9B C14B 1.394(4) . ?
C10B C11B 1.416(4) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.367(4) . ?
C12B C13B 1.429(4) . ?
C13B C14B 1.370(4) . ?
C14B H14B 0.9300 . ?
C15B H15A 0.9700 . ?
C15B H15B 0.9700 . ?
C15B C16B 1.511(4) . ?
C16B H16A 0.9700 . ?
C16B H16B 0.9700 . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C16B C17C 1.539(7) . ?
C16B C17B 1.443(11) . ?
C22B H22A 0.9600 . ?
C22B H22B 0.9600 . ?
C22B H22C 0.9600 . ?
C17C H17A 0.9700 . ?
C17C H17B 0.9700 . ?
C18C H18A 0.9700 . ?
C18C H18B 0.9700 . ?
C18C C19C 1.506(11) . ?
C19C H19A 0.9700 . ?
C19C H19B 0.9700 . ?
C20B H20A 0.9700 . ?
C20B H20B 0.9700 . ?
C20B C21B 1.51(2) . ?
C21B H21A 0.9700 . ?
C21B H21B 0.9700 . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B C19B 1.512(17) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20C H20C 0.9700 . ?
C20C H20D 0.9700 . ?
C20C C21C 1.56(3) . ?
C21C H21C 0.9700 . ?
C21C H21D 0.9700 . ?
O1A C13A 1.355(5) . ?
O1A C22A 1.419(6) . ?
O2A C12A 1.358(4) . ?
O2A C15A 1.428(4) . ?
O3A C19A 1.412(6) . ?
O3A C20A 1.422(5) . ?
N1A H1A 0.8600 . ?
N1A C6A 1.413(5) . ?
N1A C7A 1.346(5) . ?
N2A C7A 1.338(5) . ?
N2A C8A 1.347(7) . ?
N3A C8A 1.289(7) . ?
N3A C9A 1.370(5) . ?
N4A H4A 0.9800 . ?
N4A C17A 1.487(4) . ?
N4A C18A 1.493(4) . ?
N4A C21A 1.486(4) . ?
C6A C1A 1.328(13) . ?
C6A C5A 1.522(19) . ?
C6A C1C 1.463(12) . ?
C6A C5C 1.301(13) . ?
C7A C10A 1.422(5) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.418(5) . ?
C9A C14A 1.386(6) . ?
C10A C11A 1.413(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.363(5) . ?
C12A C13A 1.424(5) . ?
C13A C14A 1.361(6) . ?
C14A H14A 0.9300 . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16A 1.500(5) . ?
C16A H16E 0.9700 . ?
C16A H16F 0.9700 . ?
C16A C17A 1.516(5) . ?
C17A H17E 0.9700 . ?
C17A H17F 0.9700 . ?
C18A H18E 0.9700 . ?
C18A H18F 0.9700 . ?
C18A C19A 1.494(6) . ?
C19A H19E 0.9700 . ?
C19A H19F 0.9700 . ?
C20A H20E 0.9700 . ?
C20A H20F 0.9700 . ?
C20A C21A 1.503(6) . ?
C21A H21E 0.9700 . ?
C21A H21F 0.9700 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
Cl1C C2A 1.657(12) . ?
F1C C3A 1.373(14) . ?
C1A H1AA 0.9300 . ?
C1A C2A 1.374(16) . ?
C2A C3A 1.385(17) . ?
C3A C4A 1.390(14) . ?
C4A H4AA 0.9300 . ?
C4A C5A 1.403(18) . ?
C5A H5A 0.9300 . ?
Cl1A C4C 1.661(13) . ?
F1A C3C 1.349(11) . ?
C1C H1C 0.9300 . ?
C1C C2C 1.401(12) . ?
C2C H2C 0.9300 . ?
C2C C3C 1.366(16) . ?
C3C C4C 1.372(16) . ?
C4C C5C 1.381(12) . ?
C5C H5C 0.9300 . ?
O4A C29A 1.250(5) . ?
O5A C29A 1.259(5) . ?
O6A H6A 0.8200 . ?
O6A C24A 1.352(6) . ?
C23A C24A 1.401(6) . ?
C23A C28A 1.387(6) . ?
C23A C29A 1.481(6) . ?
C24A C25A 1.385(7) . ?
C25A H25A 0.9300 . ?
C25A C26A 1.343(10) . ?
C26A H26A 0.9300 . ?
C26A C27A 1.352(11) . ?
C27A H27A 0.9300 . ?
C27A C28A 1.377(8) . ?
C28A H28A 0.9300 . ?
O4C C29C 1.240(5) . ?
O5C C29C 1.268(5) . ?
O6C H6C 0.8200 . ?
O6C C24C 1.335(6) . ?
C23C C24C 1.389(6) . ?
C23C C28C 1.382(6) . ?
C23C C29C 1.496(4) . ?
C24C C25C 1.396(6) . ?
C25C H25C 0.9300 . ?
C25C C26C 1.357(9) . ?
C26C H26C 0.9300 . ?
C26C C27C 1.374(9) . ?
C27C H27C 0.9300 . ?
C27C C28C 1.395(6) . ?
C28C H28C 0.9300 . ?
O4D C29D 1.245(7) . ?
O5D H5D 0.8200 . ?
O5D C29D 1.225(6) . ?
O6D H6D 0.8200 . ?
O6D C24D 1.299(8) . ?
C23D C24D 1.390(7) . ?
C23D C28D 1.378(7) . ?
C23D C29D 1.482(6) . ?
C24D C25D 1.402(9) . ?
C25D H25D 0.9300 . ?
C25D C26D 1.356(13) . ?
C26D H26D 0.9300 . ?
C26D C27D 1.314(14) . ?
C27D H27D 0.9300 . ?
C27D C28D 1.363(11) . ?
C28D H28D 0.9300 . ?
O4B C29B 1.264(10) . ?
O5B C29B 1.236(11) . ?
O6B H6B 0.8200 . ?
O6B C24B 1.314(10) . ?
C23B C24B 1.383(11) . ?
C23B C28B 1.428(13) . ?
C23B C29B 1.495(12) . ?
C24B C25B 1.371(14) . ?
C25B H25B 0.9300 . ?
C25B C26B 1.397(13) . ?
C26B H26B 0.9300 . ?
C26B C27B 1.426(11) . ?
C27B H27B 0.9300 . ?
C27B C28B 1.394(11) . ?
C28B H28B 0.9300 . ?
O4F C29F 1.26(2) . ?
O5F C29F 1.182(19) . ?
O6F H6F 0.8200 . ?
O6F C24F 1.357(16) . ?
C23F C24F 1.38(2) . ?
C23F C28F 1.39(2) . ?
C23F C29F 1.498(19) . ?
C24F C25F 1.418(19) . ?
C25F H25F 0.9300 . ?
C25F C26F 1.358(19) . ?
C26F H26F 0.9300 . ?
C26F C27F 1.44(2) . ?
C27F H27F 0.9300 . ?
C27F C28F 1.43(2) . ?
C28F H28F 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
C13B O1B C22B 117.6(3) . . ?
C12B O2B C15B 117.9(2) . . ?
C19C O3B C20B 109.6(10) . . ?
C20C O3B C19B 109.2(16) . . ?
C6B N1B H1B 116.2 . . ?
C7B N1B H1B 116.2 . . ?
C7B N1B C6B 127.7(3) . . ?
C8B N2B C7B 117.7(3) . . ?
C8B N3B H3B 119.7 . . ?
C8B N3B C9B 120.7(3) . . ?
C9B N3B H3B 119.7 . . ?
C17C N4B H4B 103.3 . . ?
C18C N4B H4B 103.3 . . ?
C18C N4B C17C 115.9(5) . . ?
C18C N4B C21B 114.9(5) . . ?
C21B N4B H4B 103.3 . . ?
C21B N4B C17C 113.9(4) . . ?
C17B N4B H4BA 116.3 . . ?
C17B N4B C21C 103.2(8) . . ?
C18B N4B H4BA 116.3 . . ?
C18B N4B C17B 104.6(7) . . ?
C18B N4B C21C 97.5(7) . . ?
C21C N4B H4BA 116.3 . . ?
C2B C1B H1BA 120.1 . . ?
C2B C1B C6B 119.7(4) . . ?
C6B C1B H1BA 120.1 . . ?
C1B C2B H2B 120.0 . . ?
C3B C2B C1B 120.1(4) . . ?
C3B C2B H2B 120.0 . . ?
F1B C3B C4B 118.5(4) . . ?
C2B C3B F1B 119.8(5) . . ?
C2B C3B C4B 121.8(4) . . ?
C3B C4B Cl1B 121.1(3) . . ?
C3B C4B C5B 119.1(4) . . ?
C5B C4B Cl1B 119.8(4) . . ?
C4B C5B H5B 120.1 . . ?
C6B C5B C4B 119.7(4) . . ?
C6B C5B H5B 120.1 . . ?
C1B C6B N1B 124.1(3) . . ?
C5B C6B N1B 116.2(3) . . ?
C5B C6B C1B 119.6(3) . . ?
N1B C7B N2B 117.4(3) . . ?
N1B C7B C10B 121.1(3) . . ?
N2B C7B C10B 121.5(3) . . ?
N2B C8B N3B 125.1(3) . . ?
N2B C8B H8B 117.4 . . ?
N3B C8B H8B 117.4 . . ?
N3B C9B C10B 118.2(3) . . ?
N3B C9B C14B 120.3(3) . . ?
C14B C9B C10B 121.5(3) . . ?
C9B C10B C7B 116.7(3) . . ?
C9B C10B C11B 118.1(3) . . ?
C11B C10B C7B 125.2(3) . . ?
C10B C11B H11B 119.7 . . ?
C12B C11B C10B 120.6(3) . . ?
C12B C11B H11B 119.7 . . ?
O2B C12B C11B 125.6(3) . . ?
O2B C12B C13B 114.2(3) . . ?
C11B C12B C13B 120.2(3) . . ?
O1B C13B C12B 115.3(3) . . ?
O1B C13B C14B 124.9(3) . . ?
C14B C13B C12B 119.7(3) . . ?
C9B C14B H14B 120.1 . . ?
C13B C14B C9B 119.8(3) . . ?
C13B C14B H14B 120.1 . . ?
O2B C15B H15A 110.4 . . ?
O2B C15B H15B 110.4 . . ?
O2B C15B C16B 106.5(2) . . ?
H15A C15B H15B 108.6 . . ?
C16B C15B H15A 110.4 . . ?
C16B C15B H15B 110.4 . . ?
C15B C16B H16A 109.8 . . ?
C15B C16B H16B 109.8 . . ?
C15B C16B H16C 109.0 . . ?
C15B C16B H16D 109.0 . . ?
C15B C16B C17C 109.2(3) . . ?
H16A C16B H16B 108.3 . . ?
H16C C16B H16D 107.8 . . ?
C17C C16B H16A 109.8 . . ?
C17C C16B H16B 109.8 . . ?
C17B C16B C15B 113.0(5) . . ?
C17B C16B H16C 109.0 . . ?
C17B C16B H16D 109.0 . . ?
O1B C22B H22A 109.5 . . ?
O1B C22B H22B 109.5 . . ?
O1B C22B H22C 109.5 . . ?
H22A C22B H22B 109.5 . . ?
H22A C22B H22C 109.5 . . ?
H22B C22B H22C 109.5 . . ?
N4B C17C C16B 111.9(4) . . ?
N4B C17C H17A 109.2 . . ?
N4B C17C H17B 109.2 . . ?
C16B C17C H17A 109.2 . . ?
C16B C17C H17B 109.2 . . ?
H17A C17C H17B 107.9 . . ?
N4B C18C H18A 109.4 . . ?
N4B C18C H18B 109.4 . . ?
N4B C18C C19C 111.0(6) . . ?
H18A C18C H18B 108.0 . . ?
C19C C18C H18A 109.4 . . ?
C19C C18C H18B 109.4 . . ?
O3B C19C C18C 115.4(7) . . ?
O3B C19C H19A 108.4 . . ?
O3B C19C H19B 108.4 . . ?
C18C C19C H19A 108.4 . . ?
C18C C19C H19B 108.4 . . ?
H19A C19C H19B 107.5 . . ?
O3B C20B H20A 109.1 . . ?
O3B C20B H20B 109.1 . . ?
O3B C20B C21B 112.3(12) . . ?
H20A C20B H20B 107.9 . . ?
C21B C20B H20A 109.1 . . ?
C21B C20B H20B 109.1 . . ?
N4B C21B C20B 109.6(9) . . ?
N4B C21B H21A 109.8 . . ?
N4B C21B H21B 109.8 . . ?
C20B C21B H21A 109.8 . . ?
C20B C21B H21B 109.8 . . ?
H21A C21B H21B 108.2 . . ?
N4B C17B H17C 108.7 . . ?
N4B C17B H17D 108.7 . . ?
C16B C17B N4B 114.3(7) . . ?
C16B C17B H17C 108.7 . . ?
C16B C17B H17D 108.7 . . ?
H17C C17B H17D 107.6 . . ?
N4B C18B H18C 109.7 . . ?
N4B C18B H18D 109.7 . . ?
H18C C18B H18D 108.2 . . ?
C19B C18B N4B 109.7(10) . . ?
C19B C18B H18C 109.7 . . ?
C19B C18B H18D 109.7 . . ?
O3B C19B H19C 111.4 . . ?
O3B C19B H19D 111.4 . . ?
C18B C19B O3B 102.0(10) . . ?
C18B C19B H19C 111.4 . . ?
C18B C19B H19D 111.4 . . ?
H19C C19B H19D 109.2 . . ?
O3B C20C H20C 110.9 . . ?
O3B C20C H20D 110.9 . . ?
O3B C20C C21C 104(2) . . ?
H20C C20C H20D 108.9 . . ?
C21C C20C H20C 110.9 . . ?
C21C C20C H20D 110.9 . . ?
N4B C21C H21C 111.4 . . ?
N4B C21C H21D 111.4 . . ?
C20C C21C N4B 101.7(14) . . ?
C20C C21C H21C 111.4 . . ?
C20C C21C H21D 111.4 . . ?
H21C C21C H21D 109.3 . . ?
C13A O1A C22A 117.8(4) . . ?
C12A O2A C15A 118.0(3) . . ?
C19A O3A C20A 109.9(3) . . ?
C6A N1A H1A 116.3 . . ?
C7A N1A H1A 116.3 . . ?
C7A N1A C6A 127.4(3) . . ?
C7A N2A C8A 116.3(4) . . ?
C8A N3A C9A 119.6(4) . . ?
C17A N4A H4A 107.5 . . ?
C17A N4A C18A 110.7(3) . . ?
C18A N4A H4A 107.5 . . ?
C21A N4A H4A 107.5 . . ?
C21A N4A C17A 113.6(3) . . ?
C21A N4A C18A 109.7(3) . . ?
N1A C6A C5A 110.4(7) . . ?
N1A C6A C1C 115.1(6) . . ?
C1A C6A N1A 137.0(7) . . ?
C1A C6A C5A 112.3(9) . . ?
C5C C6A N1A 121.2(6) . . ?
C5C C6A C1C 123.6(7) . . ?
N1A C7A C10A 120.6(3) . . ?
N2A C7A N1A 117.7(4) . . ?
N2A C7A C10A 121.7(4) . . ?
N2A C8A H8A 116.6 . . ?
N3A C8A N2A 126.8(4) . . ?
N3A C8A H8A 116.6 . . ?
N3A C9A C10A 118.3(4) . . ?
N3A C9A C14A 120.2(4) . . ?
C14A C9A C10A 121.5(3) . . ?
C9A C10A C7A 117.2(3) . . ?
C11A C10A C7A 125.0(3) . . ?
C11A C10A C9A 117.8(3) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A C10A 120.2(3) . . ?
C12A C11A H11A 119.9 . . ?
O2A C12A C11A 125.5(3) . . ?
O2A C12A C13A 113.8(3) . . ?
C11A C12A C13A 120.8(3) . . ?
O1A C13A C12A 114.2(3) . . ?
O1A C13A C14A 125.9(3) . . ?
C14A C13A C12A 119.9(4) . . ?
C9A C14A H14A 120.1 . . ?
C13A C14A C9A 119.8(3) . . ?
C13A C14A H14A 120.1 . . ?
O2A C15A H15C 110.5 . . ?
O2A C15A H15D 110.5 . . ?
O2A C15A C16A 106.0(3) . . ?
H15C C15A H15D 108.7 . . ?
C16A C15A H15C 110.5 . . ?
C16A C15A H15D 110.5 . . ?
C15A C16A H16E 109.4 . . ?
C15A C16A H16F 109.4 . . ?
C15A C16A C17A 111.1(3) . . ?
H16E C16A H16F 108.0 . . ?
C17A C16A H16E 109.4 . . ?
C17A C16A H16F 109.4 . . ?
N4A C17A C16A 111.7(3) . . ?
N4A C17A H17E 109.3 . . ?
N4A C17A H17F 109.3 . . ?
C16A C17A H17E 109.3 . . ?
C16A C17A H17F 109.3 . . ?
H17E C17A H17F 107.9 . . ?
N4A C18A H18E 109.6 . . ?
N4A C18A H18F 109.6 . . ?
N4A C18A C19A 110.1(3) . . ?
H18E C18A H18F 108.1 . . ?
C19A C18A H18E 109.6 . . ?
C19A C18A H18F 109.6 . . ?
O3A C19A C18A 111.3(4) . . ?
O3A C19A H19E 109.4 . . ?
O3A C19A H19F 109.4 . . ?
C18A C19A H19E 109.4 . . ?
C18A C19A H19F 109.4 . . ?
H19E C19A H19F 108.0 . . ?
O3A C20A H20E 109.5 . . ?
O3A C20A H20F 109.5 . . ?
O3A C20A C21A 110.9(4) . . ?
H20E C20A H20F 108.1 . . ?
C21A C20A H20E 109.5 . . ?
C21A C20A H20F 109.5 . . ?
N4A C21A C20A 110.2(3) . . ?
N4A C21A H21E 109.6 . . ?
N4A C21A H21F 109.6 . . ?
C20A C21A H21E 109.6 . . ?
C20A C21A H21F 109.6 . . ?
H21E C21A H21F 108.1 . . ?
O1A C22A H22D 109.5 . . ?
O1A C22A H22E 109.5 . . ?
O1A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C6A C1A H1AA 114.9 . . ?
C6A C1A C2A 130.2(12) . . ?
C2A C1A H1AA 114.9 . . ?
C1A C2A Cl1C 120.4(11) . . ?
C1A C2A C3A 116.3(11) . . ?
C3A C2A Cl1C 123.3(10) . . ?
F1C C3A C2A 114.0(11) . . ?
F1C C3A C4A 124.6(12) . . ?
C2A C3A C4A 121.4(11) . . ?
C3A C4A H4AA 120.0 . . ?
C3A C4A C5A 119.9(14) . . ?
C5A C4A H4AA 120.0 . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A C6A 119.6(12) . . ?
C4A C5A H5A 120.2 . . ?
C6A C1C H1C 123.2 . . ?
C2C C1C C6A 113.7(10) . . ?
C2C C1C H1C 123.2 . . ?
C1C C2C H2C 119.6 . . ?
C3C C2C C1C 120.8(10) . . ?
C3C C2C H2C 119.6 . . ?
F1A C3C C2C 120.8(12) . . ?
F1A C3C C4C 116.2(14) . . ?
C2C C3C C4C 123.0(8) . . ?
C3C C4C Cl1A 126.3(9) . . ?
C3C C4C C5C 117.4(11) . . ?
C5C C4C Cl1A 116.3(10) . . ?
C6A C5C C4C 121.4(10) . . ?
C6A C5C H5C 119.3 . . ?
C4C C5C H5C 119.3 . . ?
C24A O6A H6A 109.5 . . ?
C24A C23A C29A 122.2(4) . . ?
C28A C23A C24A 116.4(4) . . ?
C28A C23A C29A 121.5(4) . . ?
O6A C24A C23A 122.0(4) . . ?
O6A C24A C25A 117.0(5) . . ?
C25A C24A C23A 121.0(5) . . ?
C24A C25A H25A 119.8 . . ?
C26A C25A C24A 120.3(7) . . ?
C26A C25A H25A 119.8 . . ?
C25A C26A H26A 119.8 . . ?
C25A C26A C27A 120.5(6) . . ?
C27A C26A H26A 119.8 . . ?
C26A C27A H27A 119.8 . . ?
C26A C27A C28A 120.4(6) . . ?
C28A C27A H27A 119.8 . . ?
C23A C28A H28A 119.3 . . ?
C27A C28A C23A 121.4(6) . . ?
C27A C28A H28A 119.3 . . ?
O4A C29A O5A 121.7(4) . . ?
O4A C29A C23A 120.3(3) . . ?
O5A C29A C23A 118.1(4) . . ?
C24C O6C H6C 109.5 . . ?
C24C C23C C29C 120.7(3) . . ?
C28C C23C C24C 118.9(3) . . ?
C28C C23C C29C 120.3(4) . . ?
O6C C24C C23C 123.0(4) . . ?
O6C C24C C25C 117.0(5) . . ?
C23C C24C C25C 120.0(4) . . ?
C24C C25C H25C 119.9 . . ?
C26C C25C C24C 120.1(5) . . ?
C26C C25C H25C 119.9 . . ?
C25C C26C H26C 119.5 . . ?
C25C C26C C27C 120.9(4) . . ?
C27C C26C H26C 119.5 . . ?
C26C C27C H27C 120.3 . . ?
C26C C27C C28C 119.4(5) . . ?
C28C C27C H27C 120.3 . . ?
C23C C28C C27C 120.6(5) . . ?
C23C C28C H28C 119.7 . . ?
C27C C28C H28C 119.7 . . ?
O4C C29C O5C 123.7(3) . . ?
O4C C29C C23C 119.0(3) . . ?
O5C C29C C23C 117.3(3) . . ?
C29D O5D H5D 109.5 . . ?
C24D O6D H6D 109.5 . . ?
C24D C23D C29D 119.7(5) . . ?
C28D C23D C24D 117.7(5) . . ?
C28D C23D C29D 122.5(5) . . ?
O6D C24D C23D 123.3(5) . . ?
O6D C24D C25D 117.1(6) . . ?
C23D C24D C25D 119.5(6) . . ?
C24D C25D H25D 120.0 . . ?
C26D C25D C24D 120.1(7) . . ?
C26D C25D H25D 120.0 . . ?
C25D C26D H26D 120.1 . . ?
C27D C26D C25D 119.7(7) . . ?
C27D C26D H26D 120.1 . . ?
C26D C27D H27D 118.7 . . ?
C26D C27D C28D 122.6(8) . . ?
C28D C27D H27D 118.7 . . ?
C23D C28D H28D 119.9 . . ?
C27D C28D C23D 120.3(8) . . ?
C27D C28D H28D 119.9 . . ?
O4D C29D C23D 117.9(5) . . ?
O5D C29D O4D 123.2(5) . . ?
O5D C29D C23D 119.0(5) . . ?
C24B O6B H6B 109.5 . . ?
C24B C23B C28B 119.7(8) . . ?
C24B C23B C29B 120.6(9) . . ?
C28B C23B C29B 119.7(7) . . ?
O6B C24B C23B 120.6(8) . . ?
O6B C24B C25B 117.4(7) . . ?
C25B C24B C23B 121.8(9) . . ?
C24B C25B H25B 120.2 . . ?
C24B C25B C26B 119.5(10) . . ?
C26B C25B H25B 120.2 . . ?
C25B C26B H26B 119.8 . . ?
C25B C26B C27B 120.4(9) . . ?
C27B C26B H26B 119.8 . . ?
C26B C27B H27B 120.4 . . ?
C28B C27B C26B 119.2(9) . . ?
C28B C27B H27B 120.4 . . ?
C23B C28B H28B 120.3 . . ?
C27B C28B C23B 119.3(8) . . ?
C27B C28B H28B 120.3 . . ?
O4B C29B C23B 117.2(8) . . ?
O5B C29B O4B 124.0(8) . . ?
O5B C29B C23B 118.7(8) . . ?
C24F O6F H6F 109.5 . . ?
C24F C23F C28F 121.3(15) . . ?
C24F C23F C29F 120.8(15) . . ?
C28F C23F C29F 117.8(16) . . ?
O6F C24F C23F 114.7(13) . . ?
O6F C24F C25F 121.0(17) . . ?
C23F C24F C25F 124.4(14) . . ?
C24F C25F H25F 122.8 . . ?
C26F C25F C24F 114.3(18) . . ?
C26F C25F H25F 122.8 . . ?
C25F C26F H26F 117.9 . . ?
C25F C26F C27F 124.2(18) . . ?
C27F C26F H26F 117.9 . . ?
C26F C27F H27F 120.4 . . ?
C28F C27F C26F 119.2(16) . . ?
C28F C27F H27F 120.4 . . ?
C23F C28F C27F 116.5(18) . . ?
C23F C28F H28F 121.8 . . ?
C27F C28F H28F 121.8 . . ?
O4F C29F C23F 119.5(16) . . ?
O5F C29F O4F 121.7(17) . . ?
O5F C29F C23F 118.6(19) . . ?

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
Cl1B C4B C5B C6B -178.7(3) . . . . ?
F1B C3B C4B Cl1B 0.3(6) . . . . ?
F1B C3B C4B C5B -179.5(4) . . . . ?
O1B C13B C14B C9B 180.0(3) . . . . ?
O2B C12B C13B O1B -0.3(4) . . . . ?
O2B C12B C13B C14B -179.3(3) . . . . ?
O2B C15B C16B C17C 158.8(4) . . . . ?
O2B C15B C16B C17B -168.4(8) . . . . ?
O3B C20B C21B N4B 51.2(15) . . . . ?
O3B C20C C21C N4B 80(2) . . . . ?
N1B C7B C10B C9B -177.7(3) . . . . ?
N1B C7B C10B C11B 2.1(5) . . . . ?
N2B C7B C10B C9B 2.5(4) . . . . ?
N2B C7B C10B C11B -177.7(3) . . . . ?
N3B C9B C10B C7B -1.4(4) . . . . ?
N3B C9B C10B C11B 178.9(3) . . . . ?
N3B C9B C14B C13B -178.7(3) . . . . ?
N4B C18C C19C O3B -54.3(10) . . . . ?
N4B C18B C19B O3B -63.0(13) . . . . ?
C1B C2B C3B F1B 178.7(4) . . . . ?
C1B C2B C3B C4B -0.2(6) . . . . ?
C2B C1B C6B N1B -176.6(3) . . . . ?
C2B C1B C6B C5B 0.2(5) . . . . ?
C2B C3B C4B Cl1B 179.2(3) . . . . ?
C2B C3B C4B C5B -0.6(6) . . . . ?
C3B C4B C5B C6B 1.1(6) . . . . ?
C4B C5B C6B N1B 176.1(3) . . . . ?
C4B C5B C6B C1B -0.9(5) . . . . ?
C6B N1B C7B N2B -0.5(5) . . . . ?
C6B N1B C7B C10B 179.7(3) . . . . ?
C6B C1B C2B C3B 0.4(6) . . . . ?
C7B N1B C6B C1B -36.1(5) . . . . ?
C7B N1B C6B C5B 146.9(3) . . . . ?
C7B N2B C8B N3B 0.6(6) . . . . ?
C7B C10B C11B C12B -179.0(3) . . . . ?
C8B N2B C7B N1B 178.1(3) . . . . ?
C8B N2B C7B C10B -2.2(5) . . . . ?
C8B N3B C9B C10B -0.1(5) . . . . ?
C8B N3B C9B C14B 179.5(4) . . . . ?
C9B N3B C8B N2B 0.5(6) . . . . ?
C9B C10B C11B C12B 0.8(4) . . . . ?
C10B C9B C14B C13B 0.9(5) . . . . ?
C10B C11B C12B O2B 179.5(3) . . . . ?
C10B C11B C12B C13B -0.9(4) . . . . ?
C11B C12B C13B O1B -179.9(3) . . . . ?
C11B C12B C13B C14B 1.1(5) . . . . ?
C12B O2B C15B C16B -174.5(3) . . . . ?
C12B C13B C14B C9B -1.1(5) . . . . ?
C14B C9B C10B C7B 179.1(3) . . . . ?
C14B C9B C10B C11B -0.7(4) . . . . ?
C15B O2B C12B C11B -4.9(4) . . . . ?
C15B O2B C12B C13B 175.6(3) . . . . ?
C15B C16B C17C N4B 170.0(4) . . . . ?
C15B C16B C17B N4B -154.1(8) . . . . ?
C22B O1B C13B C12B 179.7(3) . . . . ?
C22B O1B C13B C14B -1.4(5) . . . . ?
C17C N4B C18C C19C -172.6(6) . . . . ?
C17C N4B C21B C20B 171.3(8) . . . . ?
C18C N4B C17C C16B -85.1(8) . . . . ?
C18C N4B C21B C20B -51.7(10) . . . . ?
C19C O3B C20B C21B -53.9(15) . . . . ?
C20B O3B C19C C18C 54.5(11) . . . . ?
C21B N4B C17C C16B 51.5(9) . . . . ?
C21B N4B C18C C19C 51.2(9) . . . . ?
C17B N4B C18B C19B 172.2(11) . . . . ?
C17B N4B C21C C20C -173.7(13) . . . . ?
C18B N4B C17B C16B -151.8(13) . . . . ?
C18B N4B C21C C20C -66.6(14) . . . . ?
C19B O3B C20C C21C -80(2) . . . . ?
C20C O3B C19B C18B 71.2(18) . . . . ?
C21C N4B C17B C16B -50.2(15) . . . . ?
C21C N4B C18B C19B 66.3(12) . . . . ?
O1A C13A C14A C9A -179.7(3) . . . . ?
O2A C12A C13A O1A -2.4(5) . . . . ?
O2A C12A C13A C14A 177.9(3) . . . . ?
O2A C15A C16A C17A -178.3(3) . . . . ?
O3A C20A C21A N4A -57.9(5) . . . . ?
N1A C6A C1A C2A -175.8(10) . . . . ?
N1A C6A C5A C4A 173.3(18) . . . . ?
N1A C6A C1C C2C -175.9(7) . . . . ?
N1A C6A C5C C4C 178.1(10) . . . . ?
N1A C7A C10A C9A -179.8(3) . . . . ?
N1A C7A C10A C11A 1.6(5) . . . . ?
N2A C7A C10A C9A 2.4(5) . . . . ?
N2A C7A C10A C11A -176.2(3) . . . . ?
N3A C9A C10A C7A -0.7(4) . . . . ?
N3A C9A C10A C11A 178.0(3) . . . . ?
N3A C9A C14A C13A -177.2(3) . . . . ?
N4A C18A C19A O3A 58.1(5) . . . . ?
C6A N1A C7A N2A 1.3(5) . . . . ?
C6A N1A C7A C10A -176.6(3) . . . . ?
C6A C1A C2A Cl1C -177.1(10) . . . . ?
C6A C1A C2A C3A 3(2) . . . . ?
C6A C1C C2C C3C -1.6(15) . . . . ?
C7A N1A C6A C1A -48.8(10) . . . . ?
C7A N1A C6A C5A 138.7(13) . . . . ?
C7A N1A C6A C1C -37.0(7) . . . . ?
C7A N1A C6A C5C 146.0(9) . . . . ?
C7A N2A C8A N3A 0.0(7) . . . . ?
C7A C10A C11A C12A 176.9(3) . . . . ?
C8A N2A C7A N1A -180.0(4) . . . . ?
C8A N2A C7A C10A -2.1(5) . . . . ?
C8A N3A C9A C10A -1.2(5) . . . . ?
C8A N3A C9A C14A 176.7(4) . . . . ?
C9A N3A C8A N2A 1.7(7) . . . . ?
C9A C10A C11A C12A -1.7(5) . . . . ?
C10A C9A C14A C13A 0.7(5) . . . . ?
C10A C11A C12A O2A -177.0(3) . . . . ?
C10A C11A C12A C13A 2.5(5) . . . . ?
C11A C12A C13A O1A 178.1(3) . . . . ?
C11A C12A C13A C14A -1.7(5) . . . . ?
C12A O2A C15A C16A 166.2(3) . . . . ?
C12A C13A C14A C9A 0.0(5) . . . . ?
C14A C9A C10A C7A -178.6(3) . . . . ?
C14A C9A C10A C11A 0.1(5) . . . . ?
C15A O2A C12A C11A 1.5(5) . . . . ?
C15A O2A C12A C13A -178.1(3) . . . . ?
C15A C16A C17A N4A 152.1(3) . . . . ?
C17A N4A C18A C19A -179.9(4) . . . . ?
C17A N4A C21A C20A 178.2(3) . . . . ?
C18A N4A C17A C16A -175.1(3) . . . . ?
C18A N4A C21A C20A 53.7(4) . . . . ?
C19A O3A C20A C21A 61.3(6) . . . . ?
C20A O3A C19A C18A -61.6(6) . . . . ?
C21A N4A C17A C16A 61.0(4) . . . . ?
C21A N4A C18A C19A -53.7(4) . . . . ?
C22A O1A C13A C12A -175.4(4) . . . . ?
C22A O1A C13A C14A 4.3(6) . . . . ?
Cl1C C2A C3A F1C 1.1(17) . . . . ?
Cl1C C2A C3A C4A -177.7(12) . . . . ?
F1C C3A C4A C5A 174.9(18) . . . . ?
C1A C6A C5A C4A -1(3) . . . . ?
C1A C2A C3A F1C -178.9(12) . . . . ?
C1A C2A C3A C4A 2.3(18) . . . . ?
C2A C3A C4A C5A -6(2) . . . . ?
C3A C4A C5A C6A 6(3) . . . . ?
C5A C6A C1A C2A -3(2) . . . . ?
Cl1A C4C C5C C6A 178.0(11) . . . . ?
F1A C3C C4C Cl1A 0.7(18) . . . . ?
F1A C3C C4C C5C -178.2(13) . . . . ?
C1C C6A C5C C4C 1.3(19) . . . . ?
C1C C2C C3C F1A -179.4(12) . . . . ?
C1C C2C C3C C4C 0.0(18) . . . . ?
C2C C3C C4C Cl1A -178.8(10) . . . . ?
C2C C3C C4C C5C 2.3(19) . . . . ?
C3C C4C C5C C6A -3(2) . . . . ?
C5C C6A C1C C2C 1.0(15) . . . . ?
O6A C24A C25A C26A -178.5(6) . . . . ?
C23A C24A C25A C26A -0.3(10) . . . . ?
C24A C23A C28A C27A -0.6(7) . . . . ?
C24A C23A C29A O4A 162.5(4) . . . . ?
C24A C23A C29A O5A -16.2(6) . . . . ?
C24A C25A C26A C27A 0.6(11) . . . . ?
C25A C26A C27A C28A -1.0(11) . . . . ?
C26A C27A C28A C23A 1.0(10) . . . . ?
C28A C23A C24A O6A 178.4(5) . . . . ?
C28A C23A C24A C25A 0.2(7) . . . . ?
C28A C23A C29A O4A -17.3(6) . . . . ?
C28A C23A C29A O5A 164.0(4) . . . . ?
C29A C23A C24A O6A -1.4(7) . . . . ?
C29A C23A C24A C25A -179.6(5) . . . . ?
C29A C23A C28A C27A 179.2(5) . . . . ?
O6C C24C C25C C26C 179.0(5) . . . . ?
C23C C24C C25C C26C -2.5(7) . . . . ?
C24C C23C C28C C27C 0.2(6) . . . . ?
C24C C23C C29C O4C 174.8(3) . . . . ?
C24C C23C C29C O5C -5.8(5) . . . . ?
C24C C25C C26C C27C 2.0(8) . . . . ?
C25C C26C C27C C28C -0.5(8) . . . . ?
C26C C27C C28C C23C -0.7(7) . . . . ?
C28C C23C C24C O6C 179.8(4) . . . . ?
C28C C23C C24C C25C 1.3(6) . . . . ?
C28C C23C C29C O4C -6.9(5) . . . . ?
C28C C23C C29C O5C 172.5(3) . . . . ?
C29C C23C C24C O6C -1.8(6) . . . . ?
C29C C23C C24C C25C 179.7(4) . . . . ?
C29C C23C C28C C27C -178.1(4) . . . . ?
O6D C24D C25D C26D -177.8(7) . . . . ?
C23D C24D C25D C26D 1.0(8) . . . . ?
C24D C23D C28D C27D 1.4(8) . . . . ?
C24D C23D C29D O4D -0.2(6) . . . . ?
C24D C23D C29D O5D 180.0(4) . . . . ?
C24D C25D C26D C27D 0.9(12) . . . . ?
C25D C26D C27D C28D -1.7(14) . . . . ?
C26D C27D C28D C23D 0.5(12) . . . . ?
C28D C23D C24D O6D 176.6(5) . . . . ?
C28D C23D C24D C25D -2.1(6) . . . . ?
C28D C23D C29D O4D -176.9(5) . . . . ?
C28D C23D C29D O5D 3.3(6) . . . . ?
C29D C23D C24D O6D -0.2(7) . . . . ?
C29D C23D C24D C25D -178.9(4) . . . . ?
C29D C23D C28D C27D 178.1(6) . . . . ?
O6B C24B C25B C26B -177.0(10) . . . . ?
C23B C24B C25B C26B -1.6(19) . . . . ?
C24B C23B C28B C27B -2.4(11) . . . . ?
C24B C23B C29B O4B 179.3(8) . . . . ?
C24B C23B C29B O5B 2.3(14) . . . . ?
C24B C25B C26B C27B -0.8(19) . . . . ?
C25B C26B C27B C28B 1.5(14) . . . . ?
C26B C27B C28B C23B 0.1(11) . . . . ?
C28B C23B C24B O6B 178.5(7) . . . . ?
C28B C23B C24B C25B 3.2(14) . . . . ?
C28B C23B C29B O4B -2.8(12) . . . . ?
C28B C23B C29B O5B -179.8(9) . . . . ?
C29B C23B C24B O6B -3.6(12) . . . . ?
C29B C23B C24B C25B -178.9(11) . . . . ?
C29B C23B C28B C27B 179.7(8) . . . . ?
O6F C24F C25F C26F -177.6(14) . . . . ?
C23F C24F C25F C26F 1.3(19) . . . . ?
C24F C23F C28F C27F 1(2) . . . . ?
C24F C23F C29F O4F -172(2) . . . . ?
C24F C23F C29F O5F 13(3) . . . . ?
C24F C25F C26F C27F -4(2) . . . . ?
C25F C26F C27F C28F 5(3) . . . . ?
C26F C27F C28F C23F -3(3) . . . . ?
C28F C23F C24F O6F 179.0(15) . . . . ?
C28F C23F C24F C25F 0(2) . . . . ?
C28F C23F C29F O4F 10(3) . . . . ?
C28F C23F C29F O5F -165(2) . . . . ?
C29F C23F C24F O6F 1(2) . . . . ?
C29F C23F C24F C25F -178.3(16) . . . . ?
C29F C23F C28F C27F 179.2(17) . . . . ?

_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 3.210
_oxdiff_exptl_absorpt_empirical_full_min 0.427
