# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2301364'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hui Zhang'
;Changzhou University
China
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-03-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F N3 O3, C8 H5 O4'
_chemical_formula_sum            'C25 H24 F N3 O7'
_chemical_formula_weight         497.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.213(12)
_cell_length_b                   7.738(2)
_cell_length_c                   19.107(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.238(10)
_cell_angle_gamma                90
_cell_volume                     4636(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1802
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1012
_diffrn_reflns_av_unetI/netI     0.1116
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11880
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1930
_reflns_number_total             4079
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1932
_refine_ls_R_factor_gt           0.1017
_refine_ls_restrained_S_all      1.060
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2705
_refine_ls_wR_factor_ref         0.3495
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,
 H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C13(H13), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.06384(13) 0.7768(5) 0.20840(17) 0.0606(12) Uani 1 1 d . . . . .
O1 O -0.07791(14) 0.8528(7) -0.1568(3) 0.0625(14) Uani 1 1 d . . . . .
H1 H -0.071162 0.883912 -0.114723 0.094 Uiso 1 1 calc R U . . .
O2 O -0.04826(18) 0.7135(8) -0.2319(3) 0.0819(18) Uani 1 1 d . . . . .
O3 O -0.04214(13) 0.8570(6) -0.0247(2) 0.0519(12) Uani 1 1 d . . . . .
N1 N 0.21656(17) 0.5423(8) 0.2612(3) 0.0547(16) Uani 1 1 d . . . . .
H1A H 0.230658 0.570126 0.227825 0.082 Uiso 1 1 calc R U . . .
H1B H 0.235561 0.515623 0.301419 0.082 Uiso 1 1 calc R U . . .
N2 N 0.13036(16) 0.5824(7) 0.1824(2) 0.0421(13) Uani 1 1 d . . . . .
N3 N 0.05339(15) 0.5562(6) -0.0679(2) 0.0384(12) Uani 1 1 d . . . . .
C1 C 0.1904(2) 0.6919(10) 0.2746(4) 0.0600(19) Uani 1 1 d . . . . .
H1C H 0.208745 0.791595 0.288429 0.072 Uiso 1 1 calc R U . . .
H1D H 0.177108 0.664840 0.313914 0.072 Uiso 1 1 calc R U . . .
C2 C 0.1566(2) 0.7345(9) 0.2085(3) 0.0579(19) Uani 1 1 d . . . . .
H2A H 0.138572 0.826036 0.219570 0.069 Uiso 1 1 calc R U . . .
H2B H 0.169997 0.775790 0.171081 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1567(2) 0.4405(9) 0.1692(4) 0.0510(17) Uani 1 1 d . . . . .
H3A H 0.171166 0.472232 0.131745 0.061 Uiso 1 1 calc R U . . .
H3B H 0.138985 0.340456 0.152840 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1894(2) 0.3957(10) 0.2374(4) 0.062(2) Uani 1 1 d . . . . .
H4A H 0.174968 0.362375 0.274689 0.074 Uiso 1 1 calc R U . . .
H4B H 0.206548 0.298629 0.228499 0.074 Uiso 1 1 calc R U . . .
C5 C 0.09509(17) 0.6249(7) 0.1270(3) 0.0354(14) Uani 1 1 d . . . . .
C6 C 0.06190(19) 0.7255(7) 0.1399(3) 0.0379(14) Uani 1 1 d . . . . .
C7 C 0.02688(19) 0.7688(7) 0.0887(3) 0.0386(15) Uani 1 1 d . . . . .
H7 H 0.005099 0.833070 0.100617 0.046 Uiso 1 1 calc R U . . .
C8 C 0.02383(18) 0.7160(7) 0.0181(3) 0.0344(14) Uani 1 1 d . . . . .
C9 C 0.05589(16) 0.6108(7) 0.0026(3) 0.0303(13) Uani 1 1 d . . . . .
C10 C 0.09066(18) 0.5621(8) 0.0568(3) 0.0364(14) Uani 1 1 d . . . . .
H10 H 0.111066 0.487430 0.046477 0.044 Uiso 1 1 calc R U . . .
C11 C -0.01265(19) 0.7667(7) -0.0381(3) 0.0364(14) Uani 1 1 d . . . . .
C12 C -0.01175(18) 0.7121(8) -0.1091(3) 0.0384(15) Uani 1 1 d . . . . .
C13 C 0.02059(19) 0.6074(8) -0.1203(3) 0.0433(15) Uani 1 1 d . . . . .
H13 H 0.019620 0.569987 -0.166888 0.052 Uiso 1 1 calc R U . . .
C14 C -0.0472(2) 0.7589(9) -0.1718(4) 0.0540(18) Uani 1 1 d . . . . .
C15 C 0.08297(19) 0.4263(8) -0.0819(3) 0.0432(15) Uani 1 1 d . . . . .
H15 H 0.078278 0.309072 -0.065924 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0989(2) 0.4370(11) -0.1490(4) 0.070(2) Uani 1 1 d . . . . .
H16A H 0.089482 0.534063 -0.180782 0.084 Uiso 1 1 calc R U . . .
H16B H 0.102399 0.329642 -0.173145 0.084 Uiso 1 1 calc R U . . .
C17 C 0.1292(2) 0.4731(10) -0.0790(3) 0.0510(18) Uani 1 1 d . . . . .
H17A H 0.137959 0.591957 -0.068205 0.061 Uiso 1 1 calc R U . . .
H17B H 0.150896 0.387213 -0.060555 0.061 Uiso 1 1 calc R U . . .
O4 O 0.23499(15) 0.0784(8) 0.3376(2) 0.0766(17) Uani 1 1 d . . . . .
O5 O 0.27320(15) 0.0462(11) 0.4465(3) 0.094(2) Uani 1 1 d . . . . .
H5 H 0.270446 0.060456 0.487720 0.141 Uiso 1 1 calc R U . . .
O6 O 0.26414(15) 0.0052(8) 0.5659(3) 0.0799(19) Uani 1 1 d . . . . .
O7 O 0.21393(16) -0.0200(8) 0.6236(2) 0.0743(17) Uani 1 1 d . . . . .
C18 C 0.19564(18) 0.0400(8) 0.4268(3) 0.0384(15) Uani 1 1 d . . . . .
C19 C 0.1600(2) 0.0545(9) 0.3717(3) 0.0484(17) Uani 1 1 d . . . . .
H19 H 0.163484 0.070262 0.325115 0.058 Uiso 1 1 calc R U . . .
C20 C 0.1186(2) 0.0463(10) 0.3829(4) 0.0561(19) Uani 1 1 d . . . . .
H20 H 0.094982 0.054569 0.344532 0.067 Uiso 1 1 calc R U . . .
C21 C 0.1135(2) 0.0258(8) 0.4524(4) 0.0511(17) Uani 1 1 d . . . . .
H21 H 0.086407 0.022866 0.461623 0.061 Uiso 1 1 calc R U . . .
C22 C 0.1494(2) 0.0097(8) 0.5081(4) 0.0444(16) Uani 1 1 d . . . . .
H22 H 0.145689 -0.006171 0.554506 0.053 Uiso 1 1 calc R U . . .
C23 C 0.1903(2) 0.0160(8) 0.4976(3) 0.0423(15) Uani 1 1 d . . . . .
C24 C 0.2369(2) 0.0562(10) 0.4030(4) 0.0567(19) Uani 1 1 d . . . . .
C25 C 0.2248(2) -0.0029(9) 0.5665(3) 0.0550(19) 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
F1 C6 1.355(6) . ?
O1 H1 0.8200 . ?
O1 C14 1.312(8) . ?
O2 C14 1.194(8) . ?
O3 C11 1.253(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.487(9) . ?
N1 C4 1.441(9) . ?
N2 C2 1.468(8) . ?
N2 C3 1.446(8) . ?
N2 C5 1.403(7) . ?
N3 C9 1.396(7) . ?
N3 C13 1.339(7) . ?
N3 C15 1.452(8) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.503(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.390(8) . ?
C5 C10 1.401(8) . ?
C6 C7 1.355(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(7) . ?
C8 C9 1.399(8) . ?
C8 C11 1.453(8) . ?
C9 C10 1.392(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.428(8) . ?
C12 C13 1.374(8) . ?
C12 C14 1.498(8) . ?
C13 H13 0.9300 . ?
C15 H15 0.9800 . ?
C15 C16 1.487(9) . ?
C15 C17 1.522(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.490(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O4 C24 1.249(8) . ?
O5 H5 0.8200 . ?
O5 C24 1.273(8) . ?
O6 C25 1.272(8) . ?
O7 C25 1.227(8) . ?
C18 C19 1.374(8) . ?
C18 C23 1.414(8) . ?
C18 C24 1.505(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.400(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(9) . ?
C23 C25 1.522(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 H1 109.5 . . ?
H1A N1 H1B 108.2 . . ?
C1 N1 H1A 109.7 . . ?
C1 N1 H1B 109.7 . . ?
C4 N1 H1A 109.7 . . ?
C4 N1 H1B 109.7 . . ?
C4 N1 C1 109.9(5) . . ?
C3 N2 C2 110.7(5) . . ?
C5 N2 C2 111.9(5) . . ?
C5 N2 C3 116.9(5) . . ?
C9 N3 C15 119.5(4) . . ?
C13 N3 C9 119.6(5) . . ?
C13 N3 C15 120.4(5) . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 C2 110.9(6) . . ?
H1C C1 H1D 108.1 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
N2 C2 C1 111.1(6) . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
N2 C3 C4 110.1(5) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
N1 C4 C3 110.0(6) . . ?
N1 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 N2 121.3(5) . . ?
C6 C5 C10 116.8(5) . . ?
C10 C5 N2 121.9(5) . . ?
F1 C6 C5 118.0(5) . . ?
F1 C6 C7 118.1(5) . . ?
C7 C6 C5 123.8(5) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.3(5) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 C11 120.2(5) . . ?
C9 C8 C11 120.8(5) . . ?
N3 C9 C8 119.9(5) . . ?
C10 C9 N3 119.7(5) . . ?
C10 C9 C8 120.5(5) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.4(5) . . ?
C9 C10 H10 119.8 . . ?
O3 C11 C8 121.5(6) . . ?
O3 C11 C12 122.8(5) . . ?
C12 C11 C8 115.7(5) . . ?
C11 C12 C14 120.7(6) . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 C14 118.9(6) . . ?
N3 C13 C12 123.7(6) . . ?
N3 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
O1 C14 C12 115.7(6) . . ?
O2 C14 O1 121.1(6) . . ?
O2 C14 C12 123.2(7) . . ?
N3 C15 H15 115.4 . . ?
N3 C15 C16 119.4(6) . . ?
N3 C15 C17 120.5(5) . . ?
C16 C15 H15 115.4 . . ?
C16 C15 C17 59.4(4) . . ?
C17 C15 H15 115.4 . . ?
C15 C16 H16A 117.6 . . ?
C15 C16 H16B 117.6 . . ?
C15 C16 C17 61.5(4) . . ?
H16A C16 H16B 114.7 . . ?
C17 C16 H16A 117.6 . . ?
C17 C16 H16B 117.6 . . ?
C15 C17 H17A 117.9 . . ?
C15 C17 H17B 117.9 . . ?
C16 C17 C15 59.1(4) . . ?
C16 C17 H17A 117.9 . . ?
C16 C17 H17B 117.9 . . ?
H17A C17 H17B 115.0 . . ?
C24 O5 H5 109.5 . . ?
C19 C18 C23 118.7(5) . . ?
C19 C18 C24 113.7(5) . . ?
C23 C18 C24 127.6(5) . . ?
C18 C19 H19 118.8 . . ?
C18 C19 C20 122.5(6) . . ?
C20 C19 H19 118.8 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(6) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.1(6) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 118.6 . . ?
C23 C22 C21 122.8(6) . . ?
C23 C22 H22 118.6 . . ?
C18 C23 C25 127.9(5) . . ?
C22 C23 C18 118.3(6) . . ?
C22 C23 C25 113.8(6) . . ?
O4 C24 O5 119.2(6) . . ?
O4 C24 C18 118.0(6) . . ?
O5 C24 C18 122.7(6) . . ?
O6 C25 C23 121.3(6) . . ?
O7 C25 O6 120.0(6) . . ?
O7 C25 C23 118.6(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.82 1.77 2.525(6) 151.7 . yes
N1 H1A O4 0.89 1.85 2.726(7) 167.1 4 yes
N1 H1B O7 0.89 1.91 2.762(7) 160.8 7_556 yes
O5 H5 O6 0.82 1.61 2.387(7) 156.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C6 C7 C8 -179.2(5) . . . . ?
O3 C11 C12 C13 -177.4(6) . . . . ?
O3 C11 C12 C14 -1.1(9) . . . . ?
N1 C1 C2 N2 54.5(8) . . . . ?
N2 C3 C4 N1 -60.6(7) . . . . ?
N2 C5 C6 F1 -2.2(8) . . . . ?
N2 C5 C6 C7 -179.2(5) . . . . ?
N2 C5 C10 C9 -178.1(5) . . . . ?
N3 C9 C10 C5 175.8(5) . . . . ?
N3 C15 C16 C17 110.0(6) . . . . ?
N3 C15 C17 C16 -108.3(7) . . . . ?
C1 N1 C4 C3 59.0(7) . . . . ?
C2 N2 C3 C4 58.2(7) . . . . ?
C2 N2 C5 C6 -68.0(7) . . . . ?
C2 N2 C5 C10 114.8(6) . . . . ?
C3 N2 C2 C1 -55.9(7) . . . . ?
C3 N2 C5 C6 162.9(5) . . . . ?
C3 N2 C5 C10 -14.3(8) . . . . ?
C4 N1 C1 C2 -56.5(7) . . . . ?
C5 N2 C2 C1 171.8(5) . . . . ?
C5 N2 C3 C4 -172.1(5) . . . . ?
C5 C6 C7 C8 -2.3(9) . . . . ?
C6 C5 C10 C9 4.6(8) . . . . ?
C6 C7 C8 C9 3.7(8) . . . . ?
C6 C7 C8 C11 -177.6(5) . . . . ?
C7 C8 C9 N3 179.9(5) . . . . ?
C7 C8 C9 C10 -1.0(8) . . . . ?
C7 C8 C11 O3 -0.5(9) . . . . ?
C7 C8 C11 C12 177.4(5) . . . . ?
C8 C9 C10 C5 -3.2(8) . . . . ?
C8 C11 C12 C13 4.7(8) . . . . ?
C8 C11 C12 C14 -178.9(5) . . . . ?
C9 N3 C13 C12 -0.3(9) . . . . ?
C9 N3 C15 C16 -144.5(6) . . . . ?
C9 N3 C15 C17 -74.8(7) . . . . ?
C9 C8 C11 O3 178.1(5) . . . . ?
C9 C8 C11 C12 -4.0(8) . . . . ?
C10 C5 C6 F1 175.0(5) . . . . ?
C10 C5 C6 C7 -1.9(9) . . . . ?
C11 C8 C9 N3 1.3(8) . . . . ?
C11 C8 C9 C10 -179.7(5) . . . . ?
C11 C12 C13 N3 -2.7(9) . . . . ?
C11 C12 C14 O1 0.7(9) . . . . ?
C11 C12 C14 O2 -178.5(7) . . . . ?
C13 N3 C9 C8 1.0(8) . . . . ?
C13 N3 C9 C10 -178.0(5) . . . . ?
C13 N3 C15 C16 44.0(8) . . . . ?
C13 N3 C15 C17 113.7(6) . . . . ?
C13 C12 C14 O1 177.1(6) . . . . ?
C13 C12 C14 O2 -2.1(10) . . . . ?
C14 C12 C13 N3 -179.1(6) . . . . ?
C15 N3 C9 C8 -170.5(5) . . . . ?
C15 N3 C9 C10 10.4(8) . . . . ?
C15 N3 C13 C12 171.2(6) . . . . ?
C18 C19 C20 C21 1.1(11) . . . . ?
C18 C23 C25 O6 1.5(11) . . . . ?
C18 C23 C25 O7 178.7(6) . . . . ?
C19 C18 C23 C22 -0.5(9) . . . . ?
C19 C18 C23 C25 -179.9(6) . . . . ?
C19 C18 C24 O4 -0.8(10) . . . . ?
C19 C18 C24 O5 -180.0(7) . . . . ?
C19 C20 C21 C22 -1.6(10) . . . . ?
C20 C21 C22 C23 1.1(10) . . . . ?
C21 C22 C23 C18 0.0(9) . . . . ?
C21 C22 C23 C25 179.5(6) . . . . ?
C22 C23 C25 O6 -178.0(6) . . . . ?
C22 C23 C25 O7 -0.7(10) . . . . ?
C23 C18 C19 C20 0.0(10) . . . . ?
C23 C18 C24 O4 -179.4(7) . . . . ?
C23 C18 C24 O5 1.4(12) . . . . ?
C24 C18 C19 C20 -178.8(7) . . . . ?
C24 C18 C23 C22 178.0(6) . . . . ?
C24 C18 C23 C25 -1.4(11) . . . . ?

_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_3
_database_code_depnum_ccdc_archive 'CCDC 2301366'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hui Zhang'
;Changzhou University
China
;
_audit_update_record             
;
2024-04-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-04-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F N3 O3, 0.5(C8 H4 O4), 3(H2 O)'
_chemical_formula_sum            'C21 H27 F N3 O8'
_chemical_formula_weight         468.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   7.311(2)
_cell_length_b                   11.567(4)
_cell_length_c                   13.026(4)
_cell_angle_alpha                95.552(8)
_cell_angle_beta                 98.490(8)
_cell_angle_gamma                92.972(8)
_cell_volume                     1082.0(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1224
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_correction_T_min  0.7426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6128
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.590
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2347
_reflns_number_total             3786
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.024
_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)+(0.1638P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.2561
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-O8_$1
 2.771 with sigma of 0.005
3.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B), O8(H8A,H8B)
3.b Ternary CH refined with riding coordinates:
 C15(H15)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,
 H17B), N1(H1C,H1D)
3.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C18(H18), C20(H20)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
C1 C 0.0531(6) 0.9010(3) 0.8311(3) 0.0429(10) Uani 1 1 d . . . . .
H1A H -0.078961 0.900050 0.806557 0.052 Uiso 1 1 calc R U . . .
H1B H 0.070176 0.894291 0.905482 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1320(6) 0.7986(3) 0.7759(3) 0.0365(9) Uani 1 1 d . . . . .
H2A H 0.259858 0.793309 0.807061 0.044 Uiso 1 1 calc R U . . .
H2B H 0.062679 0.727390 0.784737 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2134(6) 0.9220(3) 0.6464(3) 0.0372(9) Uani 1 1 d . . . . .
H3A H 0.202076 0.928260 0.572015 0.045 Uiso 1 1 calc R U . . .
H3B H 0.344229 0.925122 0.674485 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1255(6) 1.0212(3) 0.6978(3) 0.0424(10) Uani 1 1 d . . . . .
H4A H 0.184933 1.094320 0.685133 0.051 Uiso 1 1 calc R U . . .
H4B H -0.004620 1.019404 0.668463 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1653(5) 0.7100(3) 0.6042(3) 0.0254(8) Uani 1 1 d . . . . .
C6 C 0.1493(5) 0.7055(3) 0.4942(3) 0.0275(8) Uani 1 1 d . . . . .
C7 C 0.1889(5) 0.6110(3) 0.4333(3) 0.0271(8) Uani 1 1 d . . . . .
H7 H 0.180154 0.613045 0.361532 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2432(5) 0.5097(3) 0.4783(3) 0.0275(8) Uani 1 1 d . . . . .
C9 C 0.2553(5) 0.5101(3) 0.5863(3) 0.0260(8) Uani 1 1 d . . . . .
C10 C 0.2179(5) 0.6094(3) 0.6476(3) 0.0259(8) Uani 1 1 d . . . . .
H10 H 0.228467 0.608094 0.719454 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3309(5) 0.3131(3) 0.5745(3) 0.0305(9) Uani 1 1 d . . . . .
H11 H 0.357690 0.246706 0.607223 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3208(5) 0.3063(3) 0.4683(3) 0.0287(8) Uani 1 1 d . . . . .
C13 C 0.2798(5) 0.4064(3) 0.4138(3) 0.0278(8) Uani 1 1 d . . . . .
C14 C 0.3450(5) 0.1924(3) 0.4106(3) 0.0361(9) Uani 1 1 d . . . . .
C15 C 0.2919(5) 0.4037(3) 0.7441(3) 0.0334(9) Uani 1 1 d . . . . .
H15 H 0.166065 0.393009 0.760646 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4272(6) 0.4737(4) 0.8260(3) 0.0438(11) Uani 1 1 d . . . . .
H16A H 0.382656 0.505535 0.888746 0.053 Uiso 1 1 calc R U . . .
H16B H 0.522774 0.522261 0.803556 0.053 Uiso 1 1 calc R U . . .
C17 C 0.4362(7) 0.3445(4) 0.8085(3) 0.0507(12) Uani 1 1 d . . . . .
H17A H 0.537304 0.314901 0.775417 0.061 Uiso 1 1 calc R U . . .
H17B H 0.397185 0.298174 0.860608 0.061 Uiso 1 1 calc R U . . .
C18 C -0.0738(5) 0.5907(3) -0.0496(3) 0.0339(9) Uani 1 1 d . . . . .
H18 H -0.123215 0.651863 -0.083364 0.041 Uiso 1 1 calc R U . . .
C19 C 0.0097(5) 0.6106(3) 0.0538(3) 0.0278(8) Uani 1 1 d . . . . .
C20 C 0.0840(5) 0.5181(3) 0.1021(3) 0.0323(9) Uani 1 1 d . . . . .
H20 H 0.141557 0.530311 0.171226 0.039 Uiso 1 1 calc R U . . .
C21 C 0.0220(5) 0.7311(3) 0.1128(3) 0.0304(9) Uani 1 1 d . . . . .
F1 F 0.0826(3) 0.79633(18) 0.44633(16) 0.0414(6) Uani 1 1 d . . . . .
N1 N 0.1443(5) 1.0130(3) 0.8120(3) 0.0374(8) Uani 1 1 d . . . . .
H1C H 0.263677 1.017086 0.839417 0.045 Uiso 1 1 calc R U . . .
H1D H 0.091767 1.072152 0.842484 0.045 Uiso 1 1 calc R U . . .
N2 N 0.1236(4) 0.8103(3) 0.6639(2) 0.0310(7) Uani 1 1 d . . . . .
N3 N 0.3046(4) 0.4097(2) 0.6335(2) 0.0279(7) Uani 1 1 d . . . . .
O1 O 0.2727(4) 0.4049(2) 0.31645(19) 0.0388(7) Uani 1 1 d . . . . .
O2 O 0.3560(4) 0.1950(2) 0.3104(2) 0.0469(8) Uani 1 1 d . . . . .
H2 H 0.323996 0.257757 0.292073 0.070 Uiso 1 1 calc R U . . .
O3 O 0.3578(5) 0.1021(2) 0.4508(2) 0.0527(8) Uani 1 1 d . . . . .
O4 O -0.0484(5) 0.8117(2) 0.0641(2) 0.0508(8) Uani 1 1 d . . . . .
O5 O 0.0946(4) 0.7433(2) 0.2067(2) 0.0446(8) Uani 1 1 d . . . . .
O6 O 0.3837(4) 0.8926(3) 0.3068(3) 0.0589(9) Uani 1 1 d G . . . .
H6A H 0.286516 0.848009 0.285836 0.088 Uiso 1 1 d G U . . .
H6B H 0.352054 0.942065 0.352459 0.088 Uiso 1 1 d G U . . .
O7 O 0.4078(6) 0.1743(3) 0.0477(3) 0.0934(14) Uani 1 1 d DG . . . .
H7A H 0.397692 0.107913 0.069862 0.140 Uiso 1 1 d G U . . .
H7B H 0.302041 0.182010 0.012891 0.140 Uiso 1 1 d G U . . .
O8 O 0.4688(5) 0.9619(3) 0.1236(3) 0.0651(10) Uani 1 1 d G . . . .
H8A H 0.420651 0.948731 0.177175 0.098 Uiso 1 1 d G U . . .
H8B H 0.419973 0.908303 0.076840 0.098 Uiso 1 1 d G 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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.511(5) . ?
C1 N1 1.486(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N2 1.471(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.495(5) . ?
C3 N2 1.471(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.486(5) . ?
C5 C6 1.416(5) . ?
C5 C10 1.389(5) . ?
C5 N2 1.406(4) . ?
C6 C7 1.357(5) . ?
C6 F1 1.350(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.410(5) . ?
C8 C9 1.396(5) . ?
C8 C13 1.452(5) . ?
C9 C10 1.397(5) . ?
C9 N3 1.405(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.369(5) . ?
C11 N3 1.333(4) . ?
C12 C13 1.439(5) . ?
C12 C14 1.483(5) . ?
C13 O1 1.259(4) . ?
C14 O2 1.323(5) . ?
C14 O3 1.215(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.487(6) . ?
C15 C17 1.487(5) . ?
C15 N3 1.466(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.497(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.386(5) . ?
C18 C20 1.366(5) 2_565 ?
C19 C20 1.387(5) . ?
C19 C21 1.517(5) . ?
C20 H20 0.9300 . ?
C21 O4 1.267(4) . ?
C21 O5 1.251(5) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
O2 H2 0.8200 . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8501 . ?
O7 H7A 0.8501 . ?
O7 H7B 0.8501 . ?
O8 H8A 0.8500 . ?
O8 H8B 0.8498 . ?

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
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 C2 111.3(3) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C2 C1 111.2(3) . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
N2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
N2 C3 C4 110.4(3) . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C4 C3 109.9(3) . . ?
N1 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C10 C5 C6 116.1(3) . . ?
C10 C5 N2 123.0(3) . . ?
N2 C5 C6 120.8(3) . . ?
C7 C6 C5 123.0(3) . . ?
F1 C6 C5 119.1(3) . . ?
F1 C6 C7 117.8(3) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C13 120.9(3) . . ?
C9 C8 C7 118.1(3) . . ?
C9 C8 C13 120.9(3) . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 N3 119.7(3) . . ?
C10 C9 N3 119.8(3) . . ?
C5 C10 C9 121.9(3) . . ?
C5 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 H11 118.2 . . ?
N3 C11 H11 118.2 . . ?
N3 C11 C12 123.6(3) . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 C14 118.6(3) . . ?
C13 C12 C14 121.0(3) . . ?
C12 C13 C8 115.5(3) . . ?
O1 C13 C8 121.9(3) . . ?
O1 C13 C12 122.6(3) . . ?
O2 C14 C12 115.3(3) . . ?
O3 C14 C12 123.8(4) . . ?
O3 C14 O2 120.9(3) . . ?
C16 C15 H15 115.5 . . ?
C16 C15 C17 60.5(3) . . ?
C17 C15 H15 115.5 . . ?
N3 C15 H15 115.5 . . ?
N3 C15 C16 120.2(3) . . ?
N3 C15 C17 118.7(3) . . ?
C15 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
C15 C16 C17 59.8(3) . . ?
H16A C16 H16B 114.9 . . ?
C17 C16 H16A 117.8 . . ?
C17 C16 H16B 117.8 . . ?
C15 C17 C16 59.8(3) . . ?
C15 C17 H17A 117.8 . . ?
C15 C17 H17B 117.8 . . ?
C16 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
H17A C17 H17B 114.9 . . ?
C19 C18 H18 119.8 . . ?
C20 C18 H18 119.8 2_565 . ?
C20 C18 C19 120.5(3) 2_565 . ?
C18 C19 C20 118.6(3) . . ?
C18 C19 C21 120.9(3) . . ?
C20 C19 C21 120.5(3) . . ?
C18 C20 C19 120.9(3) 2_565 . ?
C18 C20 H20 119.5 2_565 . ?
C19 C20 H20 119.5 . . ?
O4 C21 C19 117.3(3) . . ?
O5 C21 C19 118.1(3) . . ?
O5 C21 O4 124.6(3) . . ?
C1 N1 C4 109.5(3) . . ?
C1 N1 H1C 109.8 . . ?
C1 N1 H1D 109.8 . . ?
C4 N1 H1C 109.8 . . ?
C4 N1 H1D 109.8 . . ?
H1C N1 H1D 108.2 . . ?
C2 N2 C3 111.5(3) . . ?
C5 N2 C2 114.5(3) . . ?
C5 N2 C3 117.2(3) . . ?
C9 N3 C15 119.9(3) . . ?
C11 N3 C9 119.8(3) . . ?
C11 N3 C15 119.3(3) . . ?
C14 O2 H2 109.5 . . ?
H6A O6 H6B 104.5 . . ?
H7A O7 H7B 104.5 . . ?
H8A O8 H8B 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3A F1 0.97 2.17 2.864(5) 126.9 . yes
N1 H1C O8 0.89 1.94 2.821(5) 169.7 2_676 yes
N1 H1D O4 0.89 1.80 2.656(4) 161.5 2_576 yes
O2 H2 O1 0.82 1.77 2.530(4) 153.2 . yes
O6 H6A O5 0.85 1.91 2.743(4) 165.5 . yes
O7 H7A O8 0.85 1.96 2.769(4) 159.8 1_545 yes
O7 H7B O4 0.85 1.98 2.830(5) 175.4 2_565 yes
O8 H8A O6 0.85 1.92 2.736(5) 161.3 . yes
O8 H8B O7 0.85 2.36 2.887(6) 120.8 2_665 yes

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
C1 C2 N2 C3 54.2(4) . . . . ?
C1 C2 N2 C5 -169.8(3) . . . . ?
C2 C1 N1 C4 56.5(4) . . . . ?
C3 C4 N1 C1 -59.4(4) . . . . ?
C4 C3 N2 C2 -57.4(4) . . . . ?
C4 C3 N2 C5 168.0(3) . . . . ?
C5 C6 C7 C8 2.1(5) . . . . ?
C6 C5 C10 C9 0.9(5) . . . . ?
C6 C5 N2 C2 175.3(3) . . . . ?
C6 C5 N2 C3 -51.4(5) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C6 C7 C8 C13 177.9(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C7 C8 C9 N3 178.5(3) . . . . ?
C7 C8 C13 C12 -175.6(3) . . . . ?
C7 C8 C13 O1 3.2(5) . . . . ?
C8 C9 C10 C5 0.8(5) . . . . ?
C8 C9 N3 C11 -3.1(5) . . . . ?
C8 C9 N3 C15 -171.3(3) . . . . ?
C9 C8 C13 C12 2.5(5) . . . . ?
C9 C8 C13 O1 -178.8(3) . . . . ?
C10 C5 C6 C7 -2.3(5) . . . . ?
C10 C5 C6 F1 174.0(3) . . . . ?
C10 C5 N2 C2 -2.6(5) . . . . ?
C10 C5 N2 C3 130.7(4) . . . . ?
C10 C9 N3 C11 176.5(3) . . . . ?
C10 C9 N3 C15 8.4(5) . . . . ?
C11 C12 C13 C8 -2.7(5) . . . . ?
C11 C12 C13 O1 178.5(3) . . . . ?
C11 C12 C14 O2 -172.1(3) . . . . ?
C11 C12 C14 O3 6.5(6) . . . . ?
C12 C11 N3 C9 3.0(5) . . . . ?
C12 C11 N3 C15 171.2(3) . . . . ?
C13 C8 C9 C10 -179.3(3) . . . . ?
C13 C8 C9 N3 0.3(5) . . . . ?
C13 C12 C14 O2 10.4(5) . . . . ?
C13 C12 C14 O3 -171.0(4) . . . . ?
C14 C12 C13 C8 174.7(3) . . . . ?
C14 C12 C13 O1 -4.0(5) . . . . ?
C16 C15 N3 C9 -72.1(4) . . . . ?
C16 C15 N3 C11 119.7(4) . . . . ?
C17 C15 N3 C9 -142.7(4) . . . . ?
C17 C15 N3 C11 49.1(5) . . . . ?
C18 C19 C20 C18 -0.7(6) . . . 2_565 ?
C18 C19 C21 O4 0.7(5) . . . . ?
C18 C19 C21 O5 178.2(3) . . . . ?
C20 C18 C19 C20 0.6(6) 2_565 . . . ?
C20 C18 C19 C21 179.9(3) 2_565 . . . ?
C20 C19 C21 O4 179.9(3) . . . . ?
C20 C19 C21 O5 -2.6(5) . . . . ?
C21 C19 C20 C18 -179.9(3) . . . 2_565 ?
F1 C6 C7 C8 -174.3(3) . . . . ?
N1 C1 C2 N2 -54.1(5) . . . . ?
N2 C3 C4 N1 59.9(4) . . . . ?
N2 C5 C6 C7 179.6(3) . . . . ?
N2 C5 C6 F1 -4.0(5) . . . . ?
N2 C5 C10 C9 178.8(3) . . . . ?
N3 C9 C10 C5 -178.8(3) . . . . ?
N3 C11 C12 C13 0.0(5) . . . . ?
N3 C11 C12 C14 -177.5(3) . . . . ?
N3 C15 C16 C17 -108.0(4) . . . . ?
N3 C15 C17 C16 110.4(4) . . . . ?

_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_5
_database_code_depnum_ccdc_archive 'CCDC 2301368'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hui Zhang'
;Changzhou University
China
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-03-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C17 H19 F N3 O3), 2(C7 H5 O3), 3(C7 H6 O3), 2(H2 O)'
_chemical_formula_sum            'C69 H70 F2 N6 O23'
_chemical_formula_weight         1389.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.194(3)
_cell_length_b                   12.720(4)
_cell_length_c                   14.712(5)
_cell_angle_alpha                82.783(9)
_cell_angle_beta                 77.177(9)
_cell_angle_gamma                76.989(9)
_cell_volume                     1629.4(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9181
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.424
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3042
_reflns_number_total             5695
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         5695
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0816
_refine_ls_restrained_S_all      1.008
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2455
_refine_ls_wR_factor_ref         0.3041
_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 O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O11 \\sim O12 \\sim O13 \\sim C33 \\sim C34 \\sim C36 \\sim C37 \\sim C38 \\sim
C39: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
N3 \\sim C15 \\sim C16 \\sim C17: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 N3, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O11(0.5) O12(0.5) H12(0.5) O13(0.5) H13(0.5) C39(0.5) C40(0.5)
 H40(0.5) C36(0.5) H36(0.5) C34(0.5) C33(0.5) C38(0.5) H38(0.5) C37(0.5)
 H37(0.5)
5.a Riding coordinates:
 O9(H9), O10(H10A,H10B)
5.b Ternary CH refined with riding coordinates:
 C15(H15)
5.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,
 H16B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27),
 C28(H28), C29(H29), C30(H30), C40(H40), C36(H36), C38(H38), C37(H37)
5.e Fitted hexagon refined as free rotating group:
 C40(C36,C34,C33,C38,C37)
5.f Tetrahedral OH refined with riding coordinates:
 O6(H6)
5.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O8(H8), O12(H12), O13(H13)
;
_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
F1 F 0.8396(3) 0.89292(18) 1.06430(16) 0.0676(8) Uani 1 1 d . . . . .
O1 O 1.2043(3) 0.5363(2) 1.03809(19) 0.0588(8) Uani 1 1 d . . . . .
O2 O 1.3621(3) 0.3582(2) 0.9734(2) 0.0663(9) Uani 1 1 d . . . . .
H2 H 1.336462 0.410628 1.004851 0.100 Uiso 1 1 calc R U . . .
O3 O 1.3326(3) 0.3170(2) 0.8387(2) 0.0643(9) Uani 1 1 d . . . . .
N1 N 0.5819(4) 1.1502(3) 0.8282(2) 0.0599(10) Uani 1 1 d . . . . .
H1A H 0.501125 1.204392 0.830533 0.072 Uiso 1 1 calc R U . . .
H1B H 0.653905 1.166208 0.780410 0.072 Uiso 1 1 calc R U . . .
N2 N 0.7331(3) 0.9448(2) 0.8985(2) 0.0472(8) Uani 1 1 d . . . . .
N3 N 1.0418(4) 0.6033(3) 0.7946(2) 0.0556(9) Uani 1 1 d . U . . .
C1 C 0.5393(5) 1.0495(3) 0.8132(3) 0.0639(12) Uani 1 1 d . . . . .
H1C H 0.506731 1.057794 0.753851 0.077 Uiso 1 1 calc R U . . .
H1D H 0.454908 1.035226 0.862381 0.077 Uiso 1 1 calc R U . . .
C2 C 0.6732(4) 0.9558(3) 0.8131(3) 0.0550(11) Uani 1 1 d . . . . .
H2A H 0.641779 0.889542 0.807239 0.066 Uiso 1 1 calc R U . . .
H2B H 0.752993 0.966691 0.759504 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7732(4) 1.0453(3) 0.9132(3) 0.0531(10) Uani 1 1 d . . . . .
H3A H 0.855163 1.061179 0.862877 0.064 Uiso 1 1 calc R U . . .
H3B H 0.809136 1.036478 0.971473 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6388(5) 1.1379(3) 0.9167(3) 0.0619(12) Uani 1 1 d . . . . .
H4A H 0.558729 1.124376 0.969232 0.074 Uiso 1 1 calc R U . . .
H4B H 0.668420 1.204032 0.924963 0.074 Uiso 1 1 calc R U . . .
C5 C 0.8416(4) 0.8505(3) 0.9112(3) 0.0418(9) Uani 1 1 d . . . . .
C6 C 0.8948(4) 0.8238(3) 0.9951(3) 0.0490(10) Uani 1 1 d . . . . .
C7 C 0.9962(4) 0.7337(3) 1.0114(3) 0.0457(9) Uani 1 1 d . . . . .
H7 H 1.032303 0.722275 1.066820 0.055 Uiso 1 1 calc R U . . .
C8 C 1.0483(4) 0.6565(3) 0.9454(3) 0.0422(9) Uani 1 1 d . . . . .
C9 C 0.9940(4) 0.6789(3) 0.8617(3) 0.0411(9) Uani 1 1 d . . . . .
C10 C 0.8942(4) 0.7757(3) 0.8450(3) 0.0495(10) Uani 1 1 d . . . . .
H10 H 0.862336 0.790351 0.788111 0.059 Uiso 1 1 calc R U . . .
C11 C 1.1398(4) 0.5121(3) 0.8111(3) 0.0529(10) Uani 1 1 d . . . . .
H11 H 1.171545 0.463277 0.765154 0.063 Uiso 1 1 calc R U . . .
C12 C 1.1965(4) 0.4855(3) 0.8904(3) 0.0457(9) Uani 1 1 d . . . . .
C13 C 1.1547(4) 0.5575(3) 0.9631(3) 0.0444(9) Uani 1 1 d . . . . .
C14 C 1.3021(4) 0.3810(3) 0.8985(3) 0.0492(10) Uani 1 1 d . . . . .
C15 C 0.9928(5) 0.6285(4) 0.7034(3) 0.0684(12) Uani 1 1 d . U . . .
H15 H 1.038871 0.682211 0.659634 0.082 Uiso 1 1 calc R U . . .
C16 C 0.8390(6) 0.6271(5) 0.7030(5) 0.0919(16) Uani 1 1 d . U . . .
H16A H 0.788227 0.679938 0.660550 0.110 Uiso 1 1 calc R U . . .
H16B H 0.774012 0.610415 0.762183 0.110 Uiso 1 1 calc R U . . .
C17 C 0.9584(6) 0.5389(4) 0.6620(4) 0.0813(14) Uani 1 1 d . U . . .
H17A H 0.982761 0.538010 0.594455 0.098 Uiso 1 1 calc R U . . .
H17B H 0.968507 0.468298 0.696364 0.098 Uiso 1 1 calc R U . . .
O4 O 1.1790(5) 0.8252(4) 0.3161(3) 0.1201(18) Uani 1 1 d . . . . .
O5 O 1.0232(6) 0.7609(4) 0.2471(3) 0.1247(17) Uani 1 1 d . . . . .
O6 O 0.7324(6) 0.8037(4) 0.3116(3) 0.1265(16) Uani 1 1 d . . . . .
H6 H 0.809336 0.789537 0.270957 0.190 Uiso 1 1 calc R U . . .
C18 C 0.9180(6) 0.8338(4) 0.3931(3) 0.0726(14) Uani 1 1 d . . . . .
C19 C 0.7702(7) 0.8310(4) 0.3880(4) 0.0808(15) Uani 1 1 d . . . . .
C20 C 0.6544(7) 0.8628(6) 0.4627(4) 0.0994(19) Uani 1 1 d . . . . .
H20 H 0.554575 0.861565 0.460280 0.119 Uiso 1 1 calc R U . . .
C21 C 0.6839(8) 0.8961(5) 0.5400(4) 0.103(2) Uani 1 1 d . . . . .
H21 H 0.604592 0.915907 0.590218 0.123 Uiso 1 1 calc R U . . .
C22 C 0.8285(8) 0.9006(6) 0.5442(4) 0.1017(19) Uani 1 1 d . . . . .
H22 H 0.848301 0.924669 0.596448 0.122 Uiso 1 1 calc R U . . .
C23 C 0.9447(6) 0.8692(5) 0.4707(3) 0.0890(17) Uani 1 1 d . . . . .
H23 H 1.043747 0.871951 0.473685 0.107 Uiso 1 1 calc R U . . .
C24 C 1.0500(9) 0.8035(5) 0.3121(4) 0.099(2) Uani 1 1 d . . . . .
O7 O 0.4882(4) 0.3915(3) 0.1268(2) 0.0802(10) Uani 1 1 d . . . . .
O8 O 0.4772(4) 0.4701(3) 0.2542(2) 0.0720(9) Uani 1 1 d . . . . .
H8 H 0.431546 0.521777 0.225364 0.108 Uiso 1 1 calc R U . . .
O9 O 0.6355(4) 0.1951(3) 0.1096(3) 0.0955(12) Uani 1 1 d . . . . .
H9 H 0.586430 0.254869 0.095581 0.143 Uiso 1 1 d R U . . .
C25 C 0.6099(4) 0.2922(3) 0.2452(3) 0.0512(10) Uani 1 1 d . . . . .
C26 C 0.6639(5) 0.1990(4) 0.1960(3) 0.0678(12) Uani 1 1 d . . . . .
C27 C 0.7484(6) 0.1091(4) 0.2347(5) 0.0855(16) Uani 1 1 d . . . . .
H27 H 0.786745 0.047724 0.201675 0.103 Uiso 1 1 calc R U . . .
C28 C 0.7769(7) 0.1096(5) 0.3235(5) 0.0961(19) Uani 1 1 d . . . . .
H28 H 0.834052 0.048056 0.349670 0.115 Uiso 1 1 calc R U . . .
C29 C 0.7222(6) 0.1990(5) 0.3730(4) 0.0876(16) Uani 1 1 d . . . . .
H29 H 0.740838 0.198244 0.432742 0.105 Uiso 1 1 calc R U . . .
C30 C 0.6398(5) 0.2896(4) 0.3341(3) 0.0698(13) Uani 1 1 d . . . . .
H30 H 0.603037 0.350649 0.367591 0.084 Uiso 1 1 calc R U . . .
C31 C 0.5211(5) 0.3881(4) 0.2034(3) 0.0602(11) Uani 1 1 d . . . . .
O10 O 0.3002(4) 0.6221(2) 0.1746(2) 0.0751(9) Uani 1 1 d . . . . .
H10A H 0.272149 0.607183 0.130182 0.113 Uiso 1 1 d R U . . .
H10B H 0.230219 0.663393 0.205532 0.113 Uiso 1 1 d R U . . .
O11 O 0.7639(12) 0.3700(10) 0.5670(7) 0.136(4) Uani 0.5 1 d . U P A -1
O12 O 0.5552(13) 0.2966(8) 0.6305(8) 0.134(4) Uani 0.5 1 d . U P A -1
H12 H 0.623556 0.248791 0.645968 0.201 Uiso 0.5 1 calc R U P A -1
O13 O 0.2852(10) 0.4038(8) 0.5843(8) 0.121(3) Uani 0.5 1 d . U P A -1
H13 H 0.328190 0.362647 0.622220 0.182 Uiso 0.5 1 calc R U P A -1
C39 C 0.617(2) 0.3745(12) 0.5741(11) 0.092(5) Uani 0.5 1 d . U P A -1
C40 C 0.3631(11) 0.6203(7) 0.4266(7) 0.139(12) Uani 0.5 1 d G . P A -1
H40 H 0.306107 0.675460 0.393485 0.167 Uiso 0.5 1 calc R U P A -1
C36 C 0.2938(8) 0.5421(8) 0.4832(7) 0.103(4) Uani 0.5 1 d G U P A -1
H36 H 0.190421 0.544827 0.487916 0.124 Uiso 0.5 1 calc R U P A -1
C34 C 0.3789(9) 0.4597(7) 0.5326(6) 0.093(3) Uani 0.5 1 d G U P A -1
C33 C 0.5333(9) 0.4556(6) 0.5255(6) 0.070(2) Uani 0.5 1 d G U P A -1
C38 C 0.6026(8) 0.5339(6) 0.4690(6) 0.083(3) Uani 0.5 1 d G U P A -1
H38 H 0.705965 0.531132 0.464196 0.099 Uiso 0.5 1 calc R U P A -1
C37 C 0.5175(11) 0.6162(6) 0.4195(6) 0.100(3) Uani 0.5 1 d G U P A -1
H37 H 0.563883 0.668612 0.381625 0.119 Uiso 0.5 1 calc R U P A -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
F1 C6 1.364(4) . ?
O1 C13 1.262(4) . ?
O2 H2 0.8200 . ?
O2 C14 1.312(5) . ?
O3 C14 1.218(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.475(6) . ?
N1 C4 1.486(5) . ?
N2 C2 1.459(5) . ?
N2 C3 1.460(5) . ?
N2 C5 1.399(4) . ?
N3 C9 1.397(5) . ?
N3 C11 1.331(4) . ?
N3 C15 1.483(5) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.508(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.499(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.403(5) . ?
C5 C10 1.380(5) . ?
C6 C7 1.337(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(5) . ?
C8 C9 1.401(5) . ?
C8 C13 1.444(5) . ?
C9 C10 1.391(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.356(5) . ?
C12 C13 1.427(5) . ?
C12 C14 1.467(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.420(7) . ?
C15 C17 1.480(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.466(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O4 C24 1.292(9) . ?
O5 C24 1.250(8) . ?
O6 H6 0.8200 . ?
O6 C19 1.352(7) . ?
C18 C19 1.387(8) . ?
C18 C23 1.367(8) . ?
C18 C24 1.518(7) . ?
C19 C20 1.381(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.362(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.368(7) . ?
C23 H23 0.9300 . ?
O7 C31 1.223(5) . ?
O8 H8 0.8200 . ?
O8 C31 1.297(5) . ?
O9 H9 0.8201 . ?
O9 C26 1.362(6) . ?
C25 C26 1.402(6) . ?
C25 C30 1.389(6) . ?
C25 C31 1.455(6) . ?
C26 C27 1.367(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.389(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(8) . ?
C29 H29 0.9300 . ?
C29 C30 1.365(7) . ?
C30 H30 0.9300 . ?
O10 H10A 0.8112 . ?
O10 H10B 0.8218 . ?
O11 C39 1.32(2) . ?
O12 H12 0.8200 . ?
O12 C39 1.352(19) . ?
O13 H13 0.8200 . ?
O13 C34 1.295(11) . ?
C39 C33 1.364(13) . ?
C40 H40 0.9300 . ?
C40 C36 1.3900 . ?
C40 C37 1.3900 . ?
C36 H36 0.9300 . ?
C36 C34 1.3900 . ?
C34 C33 1.3900 . ?
C33 C38 1.3900 . ?
C38 H38 0.9300 . ?
C38 C37 1.3900 . ?
C37 H37 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 H2 109.5 . . ?
H1A N1 H1B 108.1 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 C4 110.7(3) . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C2 N2 C3 111.2(3) . . ?
C5 N2 C2 115.5(3) . . ?
C5 N2 C3 115.4(3) . . ?
C9 N3 C15 120.1(3) . . ?
C11 N3 C9 119.0(3) . . ?
C11 N3 C15 120.7(3) . . ?
N1 C1 H1C 109.6 . . ?
N1 C1 H1D 109.6 . . ?
N1 C1 C2 110.2(3) . . ?
H1C C1 H1D 108.1 . . ?
C2 C1 H1C 109.6 . . ?
C2 C1 H1D 109.6 . . ?
N2 C2 C1 111.7(3) . . ?
N2 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
N2 C3 C4 111.1(3) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
N1 C4 C3 109.5(3) . . ?
N1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C6 121.2(3) . . ?
C10 C5 N2 122.1(3) . . ?
C10 C5 C6 116.5(3) . . ?
F1 C6 C5 118.4(3) . . ?
C7 C6 F1 118.1(3) . . ?
C7 C6 C5 123.6(3) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 117.7(3) . . ?
C7 C8 C13 120.9(3) . . ?
C9 C8 C13 121.5(3) . . ?
N3 C9 C8 119.4(3) . . ?
C10 C9 N3 119.9(3) . . ?
C10 C9 C8 120.7(3) . . ?
C5 C10 C9 121.2(4) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N3 C11 H11 117.7 . . ?
N3 C11 C12 124.5(4) . . ?
C12 C11 H11 117.7 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 C14 117.9(3) . . ?
C13 C12 C14 121.5(3) . . ?
O1 C13 C8 122.1(3) . . ?
O1 C13 C12 122.9(3) . . ?
C12 C13 C8 115.0(3) . . ?
O2 C14 C12 117.5(4) . . ?
O3 C14 O2 120.8(3) . . ?
O3 C14 C12 121.7(4) . . ?
N3 C15 H15 116.6 . . ?
C16 C15 N3 117.3(5) . . ?
C16 C15 H15 116.6 . . ?
C16 C15 C17 60.7(3) . . ?
C17 C15 N3 117.4(4) . . ?
C17 C15 H15 116.6 . . ?
C15 C16 H16A 117.6 . . ?
C15 C16 H16B 117.6 . . ?
C15 C16 C17 61.7(3) . . ?
H16A C16 H16B 114.7 . . ?
C17 C16 H16A 117.6 . . ?
C17 C16 H16B 117.6 . . ?
C15 C17 H17A 118.0 . . ?
C15 C17 H17B 118.0 . . ?
C16 C17 C15 57.6(3) . . ?
C16 C17 H17A 118.0 . . ?
C16 C17 H17B 118.0 . . ?
H17A C17 H17B 115.2 . . ?
C19 O6 H6 109.5 . . ?
C19 C18 C24 121.1(6) . . ?
C23 C18 C19 119.5(4) . . ?
C23 C18 C24 119.3(6) . . ?
O6 C19 C18 123.4(5) . . ?
O6 C19 C20 118.1(6) . . ?
C20 C19 C18 118.4(6) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(6) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.3(5) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 121.3(6) . . ?
C18 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
O4 C24 C18 117.1(6) . . ?
O5 C24 O4 126.0(5) . . ?
O5 C24 C18 116.9(7) . . ?
C31 O8 H8 109.5 . . ?
C26 O9 H9 106.7 . . ?
C26 C25 C31 119.6(4) . . ?
C30 C25 C26 118.8(4) . . ?
C30 C25 C31 121.6(4) . . ?
O9 C26 C25 121.9(4) . . ?
O9 C26 C27 118.3(5) . . ?
C27 C26 C25 119.8(5) . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.8(5) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(5) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.4(5) . . ?
C30 C29 H29 120.3 . . ?
C25 C30 H30 119.4 . . ?
C29 C30 C25 121.2(5) . . ?
C29 C30 H30 119.4 . . ?
O7 C31 O8 122.0(4) . . ?
O7 C31 C25 123.1(4) . . ?
O8 C31 C25 114.9(4) . . ?
H10A O10 H10B 109.3 . . ?
C39 O12 H12 109.5 . . ?
C34 O13 H13 109.5 . . ?
O11 C39 O12 117.2(12) . . ?
O11 C39 C33 119.9(15) . . ?
O12 C39 C33 122.8(16) . . ?
C36 C40 H40 120.0 . . ?
C36 C40 C37 120.0 . . ?
C37 C40 H40 120.0 . . ?
C40 C36 H36 120.0 . . ?
C40 C36 C34 120.0 . . ?
C34 C36 H36 120.0 . . ?
O13 C34 C36 107.1(7) . . ?
O13 C34 C33 132.6(7) . . ?
C33 C34 C36 120.0 . . ?
C39 C33 C34 119.8(10) . . ?
C39 C33 C38 120.2(10) . . ?
C38 C33 C34 120.0 . . ?
C33 C38 H38 120.0 . . ?
C33 C38 C37 120.0 . . ?
C37 C38 H38 120.0 . . ?
C40 C37 H37 120.0 . . ?
C38 C37 C40 120.0 . . ?
C38 C37 H37 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C6 C7 C8 175.5(3) . . . . ?
N1 C1 C2 N2 55.3(5) . . . . ?
N2 C3 C4 N1 -58.0(5) . . . . ?
N2 C5 C6 F1 -0.9(5) . . . . ?
N2 C5 C6 C7 178.8(4) . . . . ?
N2 C5 C10 C9 -175.5(3) . . . . ?
N3 C9 C10 C5 178.1(3) . . . . ?
N3 C11 C12 C13 -1.1(7) . . . . ?
N3 C11 C12 C14 179.2(4) . . . . ?
N3 C15 C16 C17 -107.7(5) . . . . ?
N3 C15 C17 C16 107.5(5) . . . . ?
C1 N1 C4 C3 58.2(5) . . . . ?
C2 N2 C3 C4 57.0(4) . . . . ?
C2 N2 C5 C6 -172.3(4) . . . . ?
C2 N2 C5 C10 3.3(5) . . . . ?
C3 N2 C2 C1 -55.5(4) . . . . ?
C3 N2 C5 C6 55.5(5) . . . . ?
C3 N2 C5 C10 -128.9(4) . . . . ?
C4 N1 C1 C2 -56.7(4) . . . . ?
C5 N2 C2 C1 170.4(3) . . . . ?
C5 N2 C3 C4 -168.8(3) . . . . ?
C5 C6 C7 C8 -4.1(6) . . . . ?
C6 C5 C10 C9 0.4(6) . . . . ?
C6 C7 C8 C9 1.9(5) . . . . ?
C6 C7 C8 C13 -178.3(4) . . . . ?
C7 C8 C9 N3 -179.2(3) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C7 C8 C13 O1 0.3(6) . . . . ?
C7 C8 C13 C12 179.2(3) . . . . ?
C8 C9 C10 C5 -2.4(6) . . . . ?
C9 N3 C11 C12 1.0(6) . . . . ?
C9 N3 C15 C16 -73.3(5) . . . . ?
C9 N3 C15 C17 -142.6(4) . . . . ?
C9 C8 C13 O1 -179.9(3) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
C10 C5 C6 F1 -176.7(3) . . . . ?
C10 C5 C6 C7 2.9(6) . . . . ?
C11 N3 C9 C8 -1.0(6) . . . . ?
C11 N3 C9 C10 178.6(4) . . . . ?
C11 N3 C15 C16 111.3(5) . . . . ?
C11 N3 C15 C17 42.0(6) . . . . ?
C11 C12 C13 O1 179.9(4) . . . . ?
C11 C12 C13 C8 1.1(5) . . . . ?
C11 C12 C14 O2 176.8(4) . . . . ?
C11 C12 C14 O3 -3.8(6) . . . . ?
C13 C8 C9 N3 1.0(5) . . . . ?
C13 C8 C9 C10 -178.5(4) . . . . ?
C13 C12 C14 O2 -2.9(6) . . . . ?
C13 C12 C14 O3 176.5(4) . . . . ?
C14 C12 C13 O1 -0.4(6) . . . . ?
C14 C12 C13 C8 -179.2(3) . . . . ?
C15 N3 C9 C8 -176.4(4) . . . . ?
C15 N3 C9 C10 3.2(6) . . . . ?
C15 N3 C11 C12 176.4(4) . . . . ?
O6 C19 C20 C21 -177.0(6) . . . . ?
C18 C19 C20 C21 -0.2(9) . . . . ?
C19 C18 C23 C22 0.9(8) . . . . ?
C19 C18 C24 O4 168.9(5) . . . . ?
C19 C18 C24 O5 -10.3(7) . . . . ?
C19 C20 C21 C22 1.3(10) . . . . ?
C20 C21 C22 C23 -1.3(11) . . . . ?
C21 C22 C23 C18 0.2(10) . . . . ?
C23 C18 C19 O6 175.7(5) . . . . ?
C23 C18 C19 C20 -0.9(8) . . . . ?
C23 C18 C24 O4 -8.2(7) . . . . ?
C23 C18 C24 O5 172.6(5) . . . . ?
C24 C18 C19 O6 -1.3(8) . . . . ?
C24 C18 C19 C20 -177.9(5) . . . . ?
C24 C18 C23 C22 178.0(5) . . . . ?
O9 C26 C27 C28 -178.7(5) . . . . ?
C25 C26 C27 C28 1.7(8) . . . . ?
C26 C25 C30 C29 1.0(7) . . . . ?
C26 C25 C31 O7 1.1(7) . . . . ?
C26 C25 C31 O8 -179.6(4) . . . . ?
C26 C27 C28 C29 -0.3(9) . . . . ?
C27 C28 C29 C30 -0.8(9) . . . . ?
C28 C29 C30 C25 0.4(8) . . . . ?
C30 C25 C26 O9 178.3(4) . . . . ?
C30 C25 C26 C27 -2.1(7) . . . . ?
C30 C25 C31 O7 -177.3(4) . . . . ?
C30 C25 C31 O8 2.0(6) . . . . ?
C31 C25 C26 O9 -0.1(7) . . . . ?
C31 C25 C26 C27 179.5(4) . . . . ?
C31 C25 C30 C29 179.4(5) . . . . ?
O11 C39 C33 C34 179.6(10) . . . . ?
O11 C39 C33 C38 0(2) . . . . ?
O12 C39 C33 C34 0(2) . . . . ?
O12 C39 C33 C38 179.6(10) . . . . ?
O13 C34 C33 C39 6.3(14) . . . . ?
O13 C34 C33 C38 -173.9(10) . . . . ?
C39 C33 C38 C37 179.9(13) . . . . ?
C40 C36 C34 O13 175.3(8) . . . . ?
C40 C36 C34 C33 0.0 . . . . ?
C36 C40 C37 C38 0.0 . . . . ?
C36 C34 C33 C39 -179.9(13) . . . . ?
C36 C34 C33 C38 0.0 . . . . ?
C34 C33 C38 C37 0.0 . . . . ?
C33 C38 C37 C40 0.0 . . . . ?
C37 C40 C36 C34 0.0 . . . . ?

_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_4
_database_code_depnum_ccdc_archive 'CCDC 2301367'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hui Zhang'
;Changzhou University
China
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F N3 O3, C8 H2 Cl4 O4, C4 Cl2 O2'
_chemical_formula_sum            'C29 H21 Cl6 F N3 O9'
_chemical_formula_weight         787.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2235(8)
_cell_length_b                   11.3207(10)
_cell_length_c                   15.6694(14)
_cell_angle_alpha                89.989(2)
_cell_angle_beta                 75.496(2)
_cell_angle_gamma                85.944(2)
_cell_volume                     1579.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6246
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             798
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10976
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.428
_diffrn_reflns_theta_min         1.804
_diffrn_ambient_temperature      295.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6169
_reflns_number_total             7598
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.060
_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)+(0.0686P)²+0.6674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1313
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,
 H17B), N1(H1C,H1D)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O7(H7A)
;
_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
C1 C 1.1907(3) 0.5876(2) 0.13152(16) 0.0485(6) Uani 1 1 d . . . . .
H1A H 1.218935 0.510370 0.102987 0.058 Uiso 1 1 calc R U . . .
H1B H 1.144898 0.637638 0.093776 0.058 Uiso 1 1 calc R U . . .
C2 C 1.0812(3) 0.5755(2) 0.21920(16) 0.0443(5) Uani 1 1 d . . . . .
H2A H 0.991462 0.542377 0.210840 0.053 Uiso 1 1 calc R U . . .
H2B H 1.125488 0.522038 0.255657 0.053 Uiso 1 1 calc R U . . .
C3 C 1.1706(2) 0.7463(2) 0.27918(15) 0.0410(5) Uani 1 1 d . . . . .
H3A H 1.213965 0.698256 0.319098 0.049 Uiso 1 1 calc R U . . .
H3B H 1.139532 0.824073 0.306227 0.049 Uiso 1 1 calc R U . . .
C4 C 1.2867(3) 0.7573(2) 0.19205(17) 0.0475(5) Uani 1 1 d . . . . .
H4A H 1.246886 0.812972 0.155096 0.057 Uiso 1 1 calc R U . . .
H4B H 1.376202 0.787752 0.202903 0.057 Uiso 1 1 calc R U . . .
C5 C 0.9014(2) 0.71631(17) 0.31910(14) 0.0345(4) Uani 1 1 d . . . . .
C6 C 0.7718(3) 0.70270(17) 0.28807(14) 0.0360(4) Uani 1 1 d . . . . .
C7 C 0.6316(2) 0.73503(18) 0.33567(15) 0.0369(4) Uani 1 1 d . . . . .
H7 H 0.550044 0.724951 0.312161 0.044 Uiso 1 1 calc R U . . .
C8 C 0.6084(2) 0.78391(17) 0.42069(14) 0.0326(4) Uani 1 1 d . . . . .
C9 C 0.7335(2) 0.79708(16) 0.45489(13) 0.0302(4) Uani 1 1 d . . . . .
C10 C 0.8787(2) 0.76323(18) 0.40401(14) 0.0333(4) Uani 1 1 d . . . . .
H10 H 0.960744 0.772233 0.427242 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4597(2) 0.82501(17) 0.47021(15) 0.0350(4) Uani 1 1 d . . . . .
C12 C 0.4469(2) 0.87326(17) 0.55509(14) 0.0332(4) Uani 1 1 d . . . . .
C13 C 0.5717(2) 0.88251(18) 0.58620(14) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.559554 0.915287 0.642191 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2995(2) 0.92042(19) 0.60989(16) 0.0392(5) Uani 1 1 d . . . . .
C15 C 0.8392(2) 0.86253(19) 0.57581(14) 0.0355(4) Uani 1 1 d . . . . .
H15 H 0.909244 0.918752 0.544739 0.043 Uiso 1 1 calc R U . . .
C16 C 0.9089(3) 0.7578(2) 0.61289(17) 0.0447(5) Uani 1 1 d . . . . .
H16A H 0.862979 0.683146 0.613899 0.054 Uiso 1 1 calc R U . . .
H16B H 1.017347 0.750852 0.602737 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8235(3) 0.8556(2) 0.67257(16) 0.0481(5) Uani 1 1 d . . . . .
H17A H 0.725885 0.840084 0.709818 0.058 Uiso 1 1 calc R U . . .
H17B H 0.880210 0.907771 0.698659 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6121(2) 0.23437(18) 0.10351(13) 0.0339(4) Uani 1 1 d . . . . .
C19 C 0.5999(2) 0.11265(19) 0.10790(14) 0.0361(4) Uani 1 1 d . . . . .
C20 C 0.7222(3) 0.03771(19) 0.11554(14) 0.0385(4) Uani 1 1 d . . . . .
C21 C 0.8550(2) 0.0830(2) 0.12232(14) 0.0397(5) Uani 1 1 d . . . . .
C22 C 0.8661(3) 0.2041(2) 0.11979(15) 0.0415(5) Uani 1 1 d . . . . .
C23 C 0.7457(3) 0.27986(19) 0.10938(14) 0.0376(4) Uani 1 1 d . . . . .
C24 C 0.9861(3) 0.0014(2) 0.13585(17) 0.0486(6) Uani 1 1 d . . . . .
C25 C 0.4815(2) 0.31487(18) 0.09046(14) 0.0349(4) Uani 1 1 d . . . . .
C26 C 0.4721(2) 0.47487(16) 0.41796(12) 0.0278(4) Uani 1 1 d . . . . .
C27 C 0.6156(2) 0.45447(16) 0.43103(12) 0.0281(4) Uani 1 1 d . . . . .
C28 C 0.3569(2) 0.51972(16) 0.48786(13) 0.0285(4) Uani 1 1 d . . . . .
C29 C 0.4450(2) 0.45605(17) 0.32761(13) 0.0307(4) Uani 1 1 d . . . . .
Cl1 Cl 1.02912(8) 0.26093(7) 0.13121(6) 0.0679(2) Uani 1 1 d . . . . .
Cl2 Cl 0.75760(8) 0.43099(5) 0.10591(4) 0.05302(16) Uani 1 1 d . . . . .
Cl3 Cl 0.71055(9) -0.11313(5) 0.11673(5) 0.06030(19) Uani 1 1 d . . . . .
Cl4 Cl 0.43081(7) 0.05822(5) 0.10633(4) 0.04923(15) Uani 1 1 d . . . . .
Cl5 Cl 0.75862(6) 0.39841(5) 0.34422(3) 0.03989(13) Uani 1 1 d . . . . .
Cl6 Cl 0.17772(5) 0.54201(5) 0.47352(3) 0.03930(13) Uani 1 1 d . . . . .
F1 F 0.79120(17) 0.66106(13) 0.20489(9) 0.0495(3) Uani 1 1 d . . . . .
N1 N 1.3264(2) 0.6409(2) 0.14557(13) 0.0478(5) Uani 1 1 d . . . . .
H1C H 1.371317 0.592092 0.177115 0.057 Uiso 1 1 calc R U . . .
H1D H 1.390777 0.650173 0.093663 0.057 Uiso 1 1 calc R U . . .
N2 N 1.0415(2) 0.69164(16) 0.26330(13) 0.0401(4) Uani 1 1 d . . . . .
N3 N 0.71079(18) 0.84657(15) 0.53983(11) 0.0317(3) Uani 1 1 d . . . . .
O1 O 0.34607(18) 0.81881(16) 0.43817(12) 0.0490(4) Uani 1 1 d . . . . .
O2 O 0.18825(17) 0.91625(17) 0.57289(13) 0.0501(4) Uani 1 1 d . . . . .
H2 H 0.216413 0.878296 0.526402 0.075 Uiso 1 1 calc R U . . .
O3 O 0.2847(2) 0.96181(18) 0.68367(12) 0.0529(4) Uani 1 1 d . . . . .
O4 O 0.4733(2) 0.33986(18) 0.01612(11) 0.0536(5) Uani 1 1 d . . . . .
O5 O 0.38163(19) 0.35281(15) 0.15940(10) 0.0452(4) Uani 1 1 d . . . . .
H5 H 0.415250 0.344056 0.202915 0.068 Uiso 1 1 calc R U . . .
O6 O 1.0938(3) -0.0281(3) 0.07768(14) 0.0820(8) Uani 1 1 d . . . . .
O7 O 0.9739(2) -0.03352(17) 0.21730(12) 0.0525(4) Uani 1 1 d . . . . .
H7A H 0.890933 -0.010609 0.248056 0.079 Uiso 1 1 calc R U . . .
O8 O 0.43362(19) 0.34917(13) 0.30618(10) 0.0414(3) Uani 1 1 d . . . . .
O9 O 0.4366(2) 0.54367(13) 0.28280(10) 0.0415(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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.500(3) . ?
C1 N1 1.492(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N2 1.465(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(3) . ?
C3 N2 1.455(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.482(3) . ?
C5 C6 1.416(3) . ?
C5 C10 1.393(3) . ?
C5 N2 1.377(3) . ?
C6 C7 1.347(3) . ?
C6 F1 1.351(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.403(3) . ?
C8 C9 1.405(3) . ?
C8 C11 1.440(3) . ?
C9 C10 1.403(3) . ?
C9 N3 1.405(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.412(3) . ?
C11 O1 1.277(3) . ?
C12 C13 1.368(3) . ?
C12 C14 1.478(3) . ?
C13 H13 0.9300 . ?
C13 N3 1.341(3) . ?
C14 O2 1.302(3) . ?
C14 O3 1.219(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.496(3) . ?
C15 C17 1.489(3) . ?
C15 N3 1.455(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.493(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.391(3) . ?
C18 C23 1.392(3) . ?
C18 C25 1.513(3) . ?
C19 C20 1.392(3) . ?
C19 Cl4 1.723(2) . ?
C20 C21 1.389(3) . ?
C20 Cl3 1.718(2) . ?
C21 C22 1.382(3) . ?
C21 C24 1.526(3) . ?
C22 C23 1.397(3) . ?
C22 Cl1 1.726(2) . ?
C23 Cl2 1.722(2) . ?
C24 O6 1.195(3) . ?
C24 O7 1.316(3) . ?
C25 O4 1.218(3) . ?
C25 O5 1.283(3) . ?
C26 C27 1.393(3) . ?
C26 C28 1.388(3) . ?
C26 C29 1.516(3) . ?
C27 C28 1.392(3) 2_666 ?
C27 Cl5 1.7252(19) . ?
C28 Cl6 1.7242(18) . ?
C29 O8 1.274(2) . ?
C29 O9 1.224(2) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
O2 H2 0.8200 . ?
O5 H5 0.8200 . ?
O7 H7A 0.8200 . ?

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
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
N1 C1 C2 108.9(2) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N2 C2 C1 109.9(2) . . ?
N2 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
N2 C3 H3A 109.8 . . ?
N2 C3 H3B 109.8 . . ?
N2 C3 C4 109.2(2) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N1 C4 C3 111.0(2) . . ?
N1 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C10 C5 C6 116.94(19) . . ?
N2 C5 C6 119.6(2) . . ?
N2 C5 C10 123.3(2) . . ?
C7 C6 C5 123.20(19) . . ?
C7 C6 F1 118.7(2) . . ?
F1 C6 C5 118.02(19) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.03(19) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 118.77(19) . . ?
C7 C8 C11 120.49(19) . . ?
C9 C8 C11 120.67(19) . . ?
C10 C9 C8 120.25(19) . . ?
C10 C9 N3 120.79(18) . . ?
N3 C9 C8 118.96(17) . . ?
C5 C10 C9 120.78(19) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C8 116.65(18) . . ?
O1 C11 C8 121.3(2) . . ?
O1 C11 C12 122.04(19) . . ?
C11 C12 C14 120.51(19) . . ?
C13 C12 C11 120.55(19) . . ?
C13 C12 C14 118.9(2) . . ?
C12 C13 H13 118.4 . . ?
N3 C13 C12 123.1(2) . . ?
N3 C13 H13 118.4 . . ?
O2 C14 C12 115.0(2) . . ?
O3 C14 C12 122.0(2) . . ?
O3 C14 O2 122.9(2) . . ?
C16 C15 H15 115.5 . . ?
C17 C15 H15 115.5 . . ?
C17 C15 C16 60.03(16) . . ?
N3 C15 H15 115.5 . . ?
N3 C15 C16 118.76(18) . . ?
N3 C15 C17 120.20(18) . . ?
C15 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
H16A C16 H16B 114.9 . . ?
C17 C16 C15 59.78(15) . . ?
C17 C16 H16A 117.8 . . ?
C17 C16 H16B 117.8 . . ?
C15 C17 C16 60.19(15) . . ?
C15 C17 H17A 117.8 . . ?
C15 C17 H17B 117.8 . . ?
C16 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
H17A C17 H17B 114.9 . . ?
C19 C18 C23 119.31(19) . . ?
C19 C18 C25 119.57(19) . . ?
C23 C18 C25 121.11(19) . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 Cl4 118.79(16) . . ?
C20 C19 Cl4 121.37(17) . . ?
C19 C20 Cl3 120.16(18) . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 Cl3 118.90(17) . . ?
C20 C21 C24 121.0(2) . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 C24 119.8(2) . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 Cl1 119.32(18) . . ?
C23 C22 Cl1 120.33(18) . . ?
C18 C23 C22 120.4(2) . . ?
C18 C23 Cl2 118.68(17) . . ?
C22 C23 Cl2 120.95(18) . . ?
O6 C24 C21 123.2(2) . . ?
O6 C24 O7 121.6(2) . . ?
O7 C24 C21 115.14(19) . . ?
O4 C25 C18 119.70(19) . . ?
O4 C25 O5 122.5(2) . . ?
O5 C25 C18 117.81(18) . . ?
C27 C26 C29 120.46(16) . . ?
C28 C26 C27 118.61(17) . . ?
C28 C26 C29 120.81(16) . . ?
C26 C27 Cl5 118.59(15) . . ?
C28 C27 C26 120.57(17) 2_666 . ?
C28 C27 Cl5 120.84(14) 2_666 . ?
C26 C28 C27 120.81(17) . 2_666 ?
C26 C28 Cl6 119.16(15) . . ?
C27 C28 Cl6 120.03(14) 2_666 . ?
O8 C29 C26 115.81(16) . . ?
O9 C29 C26 117.48(18) . . ?
O9 C29 O8 126.71(19) . . ?
C1 N1 H1C 109.3 . . ?
C1 N1 H1D 109.3 . . ?
C4 N1 C1 111.40(18) . . ?
C4 N1 H1C 109.3 . . ?
C4 N1 H1D 109.3 . . ?
H1C N1 H1D 108.0 . . ?
C3 N2 C2 112.83(18) . . ?
C5 N2 C2 120.17(18) . . ?
C5 N2 C3 120.01(18) . . ?
C9 N3 C15 119.73(16) . . ?
C13 N3 C9 119.97(17) . . ?
C13 N3 C15 120.27(17) . . ?
C14 O2 H2 109.5 . . ?
C25 O5 H5 109.5 . . ?
C24 O7 H7A 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
C1 C2 N2 C3 -60.1(3) . . . . ?
C1 C2 N2 C5 149.2(2) . . . . ?
C2 C1 N1 C4 -57.5(2) . . . . ?
C3 C4 N1 C1 56.2(3) . . . . ?
C4 C3 N2 C2 57.2(2) . . . . ?
C4 C3 N2 C5 -152.0(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C5 C10 C9 -1.2(3) . . . . ?
C6 C5 N2 C2 -55.4(3) . . . . ?
C6 C5 N2 C3 155.9(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C11 176.45(19) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C7 C8 C9 N3 179.67(18) . . . . ?
C7 C8 C11 C12 -179.81(18) . . . . ?
C7 C8 C11 O1 -0.4(3) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
C8 C9 N3 C13 -1.3(3) . . . . ?
C8 C9 N3 C15 -179.08(17) . . . . ?
C8 C11 C12 C13 1.7(3) . . . . ?
C8 C11 C12 C14 178.48(17) . . . . ?
C9 C8 C11 C12 -2.8(3) . . . . ?
C9 C8 C11 O1 176.58(19) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
C10 C5 C6 F1 177.85(18) . . . . ?
C10 C5 N2 C2 129.6(2) . . . . ?
C10 C5 N2 C3 -19.1(3) . . . . ?
C10 C9 N3 C13 177.49(18) . . . . ?
C10 C9 N3 C15 -0.3(3) . . . . ?
C11 C8 C9 C10 -176.18(18) . . . . ?
C11 C8 C9 N3 2.6(3) . . . . ?
C11 C12 C13 N3 -0.5(3) . . . . ?
C11 C12 C14 O2 -1.7(3) . . . . ?
C11 C12 C14 O3 179.4(2) . . . . ?
C12 C13 N3 C9 0.3(3) . . . . ?
C12 C13 N3 C15 178.02(19) . . . . ?
C13 C12 C14 O2 175.06(19) . . . . ?
C13 C12 C14 O3 -3.8(3) . . . . ?
C14 C12 C13 N3 -177.31(18) . . . . ?
C16 C15 N3 C9 -79.2(2) . . . . ?
C16 C15 N3 C13 103.0(2) . . . . ?
C17 C15 N3 C9 -149.3(2) . . . . ?
C17 C15 N3 C13 32.9(3) . . . . ?
C18 C19 C20 C21 2.5(3) . . . . ?
C18 C19 C20 Cl3 -177.48(16) . . . . ?
C19 C18 C23 C22 -0.2(3) . . . . ?
C19 C18 C23 Cl2 -178.79(16) . . . . ?
C19 C18 C25 O4 -90.5(3) . . . . ?
C19 C18 C25 O5 88.5(3) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C19 C20 C21 C24 176.6(2) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C20 C21 C22 Cl1 178.25(17) . . . . ?
C20 C21 C24 O6 101.4(3) . . . . ?
C20 C21 C24 O7 -79.7(3) . . . . ?
C21 C22 C23 C18 1.5(3) . . . . ?
C21 C22 C23 Cl2 -179.89(17) . . . . ?
C22 C21 C24 O6 -80.9(4) . . . . ?
C22 C21 C24 O7 98.0(3) . . . . ?
C23 C18 C19 C20 -1.8(3) . . . . ?
C23 C18 C19 Cl4 176.66(16) . . . . ?
C23 C18 C25 O4 88.2(3) . . . . ?
C23 C18 C25 O5 -92.9(3) . . . . ?
C24 C21 C22 C23 -178.6(2) . . . . ?
C24 C21 C22 Cl1 0.5(3) . . . . ?
C25 C18 C19 C20 176.85(19) . . . . ?
C25 C18 C19 Cl4 -4.7(3) . . . . ?
C25 C18 C23 C22 -178.81(19) . . . . ?
C25 C18 C23 Cl2 2.6(3) . . . . ?
C27 C26 C28 C27 1.0(3) . . . 2_666 ?
C27 C26 C28 Cl6 -178.41(14) . . . . ?
C27 C26 C29 O8 80.1(2) . . . . ?
C27 C26 C29 O9 -99.6(2) . . . . ?
C28 C26 C27 C28 -1.0(3) . . . 2_666 ?
C28 C26 C27 Cl5 179.85(14) . . . . ?
C28 C26 C29 O8 -103.9(2) . . . . ?
C28 C26 C29 O9 76.3(2) . . . . ?
C29 C26 C27 C28 175.06(17) . . . 2_666 ?
C29 C26 C27 Cl5 -4.1(2) . . . . ?
C29 C26 C28 C27 -175.04(17) . . . 2_666 ?
C29 C26 C28 Cl6 5.6(2) . . . . ?
Cl1 C22 C23 C18 -177.57(16) . . . . ?
Cl1 C22 C23 Cl2 1.0(3) . . . . ?
Cl3 C20 C21 C22 178.83(17) . . . . ?
Cl3 C20 C21 C24 -3.4(3) . . . . ?
Cl4 C19 C20 C21 -175.92(17) . . . . ?
Cl4 C19 C20 Cl3 4.1(3) . . . . ?
F1 C6 C7 C8 -176.94(18) . . . . ?
N1 C1 C2 N2 58.1(3) . . . . ?
N2 C3 C4 N1 -54.6(3) . . . . ?
N2 C5 C6 C7 -173.8(2) . . . . ?
N2 C5 C6 F1 2.6(3) . . . . ?
N2 C5 C10 C9 173.91(19) . . . . ?
N3 C9 C10 C5 -178.73(18) . . . . ?
N3 C15 C16 C17 -110.2(2) . . . . ?
N3 C15 C17 C16 107.9(2) . . . . ?
O1 C11 C12 C13 -177.6(2) . . . . ?
O1 C11 C12 C14 -0.9(3) . . . . ?

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 2301365'
loop_
_audit_author_name
_audit_author_address
'Zhi-Hui Zhang'
;Changzhou University
China
;
_audit_update_record             
;
2024-04-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-04-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C17 H19 F N3 O3), 2(C8 H4 O4), 5(H2 O)'
_chemical_formula_sum            'C84 H94 F4 N12 O25'
_chemical_formula_weight         1747.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5368(12)
_cell_length_b                   13.7042(16)
_cell_length_c                   15.0079(17)
_cell_angle_alpha                84.737(2)
_cell_angle_beta                 86.232(2)
_cell_angle_gamma                69.254(2)
_cell_volume                     2016.8(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5753
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             918
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.784
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14122
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         1.593
_diffrn_ambient_temperature      295.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.784
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6935
_reflns_number_total             9715
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         9715
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1651P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2345
_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 O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O11) \\sim Ueq, Uanis(O11A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(O11A)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(O11)=Sof(H11A)=Sof(H11B)=FVAR(1)
 Fixed Sof: O13(0.5) H13A(0.5) H13B(0.5)
4.a Riding coordinates:
 O11(H11A,H11B), O11A(H11C,H11D), O12(H12A,H12B), O13(H13A,H13B)
4.b Ternary CH refined with riding coordinates:
 C14(H14), C31(H31)
4.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C15(H15A,
 H15B), C16(H16A,H16B), N4(H4C,H4D), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C32(H32A,H32B), C33(H33A,H33B)
4.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C13(H13), C24(H24), C27(H27), C30(H30), C37(H37), C39(H39),
 C40(H40), C41(H41)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6A)
;
_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
F1 F 0.57833(11) 0.70193(14) 0.40503(10) 0.0652(4) Uani 1 1 d . . . . .
O1 O 0.89281(16) 0.64755(12) 0.65387(9) 0.0475(4) Uani 1 1 d . . . . .
O2 O 1.10969(19) 0.60174(14) 0.74082(10) 0.0577(4) Uani 1 1 d . . . . .
H2 H 1.029671 0.617405 0.729078 0.086 Uiso 1 1 calc R U . . .
O3 O 1.30716(18) 0.55069(15) 0.66817(12) 0.0639(5) Uani 1 1 d . . . . .
N1 N 0.57704(18) 0.70179(16) 0.09530(11) 0.0475(4) Uani 1 1 d . . . . .
H1A H 0.598650 0.748352 0.058061 0.057 Uiso 1 1 calc R U . . .
H1B H 0.519672 0.680987 0.067909 0.057 Uiso 1 1 calc R U . . .
N2 N 0.72580(16) 0.68550(13) 0.24768(11) 0.0393(4) Uani 1 1 d . . . . .
N3 N 1.12959(14) 0.59502(11) 0.42269(10) 0.0313(3) Uani 1 1 d . . . . .
C1 C 0.7030(2) 0.6095(2) 0.11532(15) 0.0513(5) Uani 1 1 d . . . . .
H1C H 0.748152 0.582087 0.059769 0.062 Uiso 1 1 calc R U . . .
H1D H 0.679066 0.554740 0.149835 0.062 Uiso 1 1 calc R U . . .
C2 C 0.7979(2) 0.64157(17) 0.16756(12) 0.0408(4) Uani 1 1 d . . . . .
H2A H 0.877641 0.581234 0.182969 0.049 Uiso 1 1 calc R U . . .
H2B H 0.827179 0.692932 0.131819 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6083(2) 0.78046(17) 0.22702(16) 0.0497(5) Uani 1 1 d . . . . .
H3A H 0.637632 0.831600 0.191040 0.060 Uiso 1 1 calc R U . . .
H3B H 0.565258 0.810872 0.282034 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5090(2) 0.7523(2) 0.17668(15) 0.0522(6) Uani 1 1 d . . . . .
H4A H 0.474785 0.705064 0.214348 0.063 Uiso 1 1 calc R U . . .
H4B H 0.432722 0.814939 0.160368 0.063 Uiso 1 1 calc R U . . .
C5 C 0.78965(18) 0.67280(13) 0.32777(12) 0.0325(4) Uani 1 1 d . . . . .
C6 C 0.92989(17) 0.64075(14) 0.33327(11) 0.0317(4) Uani 1 1 d . . . . .
H6 H 0.984750 0.629097 0.281356 0.038 Uiso 1 1 calc R U . . .
C7 C 0.98886(16) 0.62594(13) 0.41676(11) 0.0280(3) Uani 1 1 d . . . . .
C8 C 0.90796(18) 0.64366(13) 0.49583(11) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.76685(19) 0.67237(15) 0.48959(12) 0.0368(4) Uani 1 1 d . . . . .
H9 H 0.711132 0.683533 0.541137 0.044 Uiso 1 1 calc R U . . .
C10 C 0.71219(18) 0.68375(16) 0.40898(13) 0.0386(4) Uani 1 1 d . . . . .
C11 C 0.9665(2) 0.63054(13) 0.58275(12) 0.0334(4) Uani 1 1 d . . . . .
C12 C 1.1101(2) 0.59808(14) 0.58240(12) 0.0349(4) Uani 1 1 d . . . . .
C13 C 1.18436(19) 0.58065(14) 0.50357(12) 0.0346(4) Uani 1 1 d . . . . .
H13 H 1.278473 0.557450 0.505908 0.041 Uiso 1 1 calc R U . . .
C14 C 1.21652(18) 0.56900(16) 0.34219(13) 0.0385(4) Uani 1 1 d . . . . .
H14 H 1.220547 0.504983 0.316007 0.046 Uiso 1 1 calc R U . . .
C15 C 1.2262(2) 0.65529(18) 0.27715(15) 0.0476(5) Uani 1 1 d . . . . .
H15A H 1.175311 0.726612 0.291438 0.057 Uiso 1 1 calc R U . . .
H15B H 1.233620 0.643751 0.213913 0.057 Uiso 1 1 calc R U . . .
C16 C 1.3443(2) 0.5931(2) 0.33370(17) 0.0538(6) Uani 1 1 d . . . . .
H16A H 1.422950 0.544109 0.304571 0.065 Uiso 1 1 calc R U . . .
H16B H 1.364639 0.626972 0.382098 0.065 Uiso 1 1 calc R U . . .
C17 C 1.1861(2) 0.58078(16) 0.66650(14) 0.0441(5) Uani 1 1 d . . . . .
F2 F 0.39094(11) 0.81702(12) 0.51666(9) 0.0569(4) Uani 1 1 d . . . . .
O4 O -0.01660(15) 0.88852(11) 0.33812(9) 0.0428(3) Uani 1 1 d . . . . .
O5 O -0.42387(17) 0.96800(19) 0.39697(13) 0.0778(6) Uani 1 1 d . . . . .
O6 O -0.25894(17) 0.93841(13) 0.29379(10) 0.0535(4) Uani 1 1 d . . . . .
H6A H -0.176600 0.925092 0.291856 0.080 Uiso 1 1 calc R U . . .
N4 N 0.50706(18) 0.75569(15) 0.83235(12) 0.0485(5) Uani 1 1 d . . . . .
H4C H 0.503170 0.696001 0.858973 0.058 Uiso 1 1 calc R U . . .
H4D H 0.567420 0.772704 0.860250 0.058 Uiso 1 1 calc R U . . .
N5 N 0.31592(15) 0.80106(13) 0.69596(10) 0.0357(4) Uani 1 1 d . . . . .
N6 N -0.14869(14) 0.89807(11) 0.60112(9) 0.0297(3) Uani 1 1 d . . . . .
C18 C 0.3720(2) 0.83902(17) 0.84039(13) 0.0454(5) Uani 1 1 d . . . . .
H18A H 0.378558 0.905773 0.817901 0.054 Uiso 1 1 calc R U . . .
H18B H 0.342502 0.843648 0.902959 0.054 Uiso 1 1 calc R U . . .
C19 C 0.2685(2) 0.81663(18) 0.78824(13) 0.0426(5) Uani 1 1 d . . . . .
H19A H 0.253326 0.754456 0.815334 0.051 Uiso 1 1 calc R U . . .
H19B H 0.182858 0.874772 0.790225 0.051 Uiso 1 1 calc R U . . .
C20 C 0.44729(18) 0.71474(17) 0.69027(14) 0.0434(5) Uani 1 1 d . . . . .
H20A H 0.475481 0.704197 0.627979 0.052 Uiso 1 1 calc R U . . .
H20B H 0.438361 0.650608 0.718017 0.052 Uiso 1 1 calc R U . . .
C21 C 0.5522(2) 0.7404(2) 0.73714(16) 0.0508(5) Uani 1 1 d . . . . .
H21A H 0.639067 0.683783 0.733548 0.061 Uiso 1 1 calc R U . . .
H21B H 0.562887 0.803613 0.708645 0.061 Uiso 1 1 calc R U . . .
C22 C 0.22176(17) 0.81986(13) 0.63045(11) 0.0303(4) Uani 1 1 d . . . . .
C23 C 0.26152(17) 0.82608(14) 0.53897(12) 0.0334(4) Uani 1 1 d . . . . .
C24 C 0.17461(19) 0.84476(14) 0.47151(12) 0.0335(4) Uani 1 1 d . . . . .
H24 H 0.207305 0.841950 0.412365 0.040 Uiso 1 1 calc R U . . .
C25 C 0.03501(17) 0.86838(12) 0.49097(11) 0.0275(3) Uani 1 1 d . . . . .
C26 C -0.01010(16) 0.87027(12) 0.58116(11) 0.0264(3) Uani 1 1 d . . . . .
C27 C 0.08413(17) 0.84266(13) 0.64959(11) 0.0289(3) Uani 1 1 d . . . . .
H27 H 0.053452 0.839626 0.708955 0.035 Uiso 1 1 calc R U . . .
C28 C -0.05876(18) 0.89193(13) 0.41897(11) 0.0301(4) Uani 1 1 d . . . . .
C29 C -0.19826(18) 0.91815(14) 0.44588(12) 0.0341(4) Uani 1 1 d . . . . .
C30 C -0.23688(18) 0.92003(14) 0.53491(12) 0.0341(4) Uani 1 1 d . . . . .
H30 H -0.328755 0.937375 0.550339 0.041 Uiso 1 1 calc R U . . .
C31 C -0.19737(18) 0.89755(16) 0.69437(12) 0.0357(4) Uani 1 1 d . . . . .
H31 H -0.186785 0.828706 0.724453 0.043 Uiso 1 1 calc R U . . .
C32 C -0.3205(2) 0.98562(19) 0.72148(15) 0.0490(5) Uani 1 1 d . . . . .
H32A H -0.383134 0.969746 0.765683 0.059 Uiso 1 1 calc R U . . .
H32B H -0.362678 1.040740 0.676032 0.059 Uiso 1 1 calc R U . . .
C33 C -0.18396(19) 0.97679(17) 0.75188(13) 0.0417(4) Uani 1 1 d . . . . .
H33A H -0.143645 1.026434 0.724676 0.050 Uiso 1 1 calc R U . . .
H33B H -0.164109 0.955415 0.814359 0.050 Uiso 1 1 calc R U . . .
C34 C -0.3042(2) 0.94343(17) 0.37756(14) 0.0455(5) Uani 1 1 d . . . . .
O7 O 1.27649(15) 0.58573(14) 0.00575(13) 0.0626(5) Uani 1 1 d . . . . .
O8 O 1.34506(17) 0.71467(16) 0.03002(14) 0.0693(5) Uani 1 1 d . . . . .
O9 O 0.81203(17) 0.71957(15) -0.13599(11) 0.0601(4) Uani 1 1 d . . . . .
O10 O 0.65014(15) 0.82333(15) -0.04941(13) 0.0649(5) Uani 1 1 d . . . . .
C35 C 1.25588(19) 0.67808(17) 0.01757(13) 0.0422(5) Uani 1 1 d . . . . .
C36 C 1.11030(19) 0.75399(16) 0.01942(13) 0.0384(4) Uani 1 1 d . . . . .
C37 C 1.01306(18) 0.73525(15) -0.02827(12) 0.0352(4) Uani 1 1 d . . . . .
H37 H 1.038010 0.677369 -0.062118 0.042 Uiso 1 1 calc R U . . .
C38 C 0.87867(18) 0.80309(15) -0.02526(12) 0.0374(4) Uani 1 1 d . . . . .
C39 C 0.8440(2) 0.88863(19) 0.02471(18) 0.0570(6) Uani 1 1 d . . . . .
H39 H 0.754482 0.934310 0.027306 0.068 Uiso 1 1 calc R U . . .
C40 C 0.9418(3) 0.9073(2) 0.0713(2) 0.0729(8) Uani 1 1 d . . . . .
H40 H 0.917300 0.965024 0.105413 0.087 Uiso 1 1 calc R U . . .
C41 C 1.0745(3) 0.8409(2) 0.06726(18) 0.0588(6) Uani 1 1 d . . . . .
H41 H 1.140186 0.854917 0.096975 0.071 Uiso 1 1 calc R U . . .
C42 C 0.77484(19) 0.77931(17) -0.07536(14) 0.0415(4) Uani 1 1 d . . . . .
O11 O 0.1384(7) 0.4944(3) 0.1502(4) 0.0908(18) Uani 0.759(17) 1 d . U P A 1
H11A H 0.152471 0.430017 0.145806 0.136 Uiso 0.759(17) 1 d R U P A 1
H11B H 0.181751 0.511577 0.105446 0.136 Uiso 0.759(17) 1 d R U P A 1
O11A O 0.082(2) 0.4981(13) 0.098(3) 0.141(10) Uani 0.241(17) 1 d . U P A 2
H11C H 0.111253 0.431725 0.105758 0.212 Uiso 0.241(17) 1 d R U P A 2
H11D H 0.144903 0.512075 0.067128 0.212 Uiso 0.241(17) 1 d R U P A 2
O12 O 0.48866(19) 0.44871(15) 0.11318(14) 0.0727(6) Uani 1 1 d . . . . .
H12A H 0.554304 0.435440 0.077876 0.109 Uiso 1 1 d R U . . .
H12B H 0.412564 0.486110 0.097496 0.109 Uiso 1 1 d R U . . .
O13 O 0.4809(5) 0.9614(4) 0.0567(4) 0.115(2) Uani 0.5 1 d . . P . .
H13A H 0.549793 0.930568 0.027510 0.172 Uiso 0.5 1 d R U P . .
H13B H 0.462613 1.028028 0.046790 0.172 Uiso 0.5 1 d R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.347(2) . ?
O1 C11 1.267(2) . ?
O2 H2 0.8200 . ?
O2 C17 1.324(3) . ?
O3 C17 1.195(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.499(3) . ?
N1 C4 1.474(3) . ?
N2 C2 1.440(2) . ?
N2 C3 1.469(3) . ?
N2 C5 1.383(2) . ?
N3 C7 1.397(2) . ?
N3 C13 1.346(2) . ?
N3 C14 1.459(2) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.502(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.390(2) . ?
C5 C10 1.411(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.401(2) . ?
C7 C8 1.402(2) . ?
C8 C9 1.404(3) . ?
C8 C11 1.449(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.347(3) . ?
C11 C12 1.418(3) . ?
C12 C13 1.366(3) . ?
C12 C17 1.495(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.491(3) . ?
C14 C16 1.491(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.500(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
F2 C23 1.347(2) . ?
O4 C28 1.264(2) . ?
O5 C34 1.207(3) . ?
O6 H6A 0.8200 . ?
O6 C34 1.314(3) . ?
N4 H4C 0.8900 . ?
N4 H4D 0.8900 . ?
N4 C18 1.482(3) . ?
N4 C21 1.486(3) . ?
N5 C19 1.450(2) . ?
N5 C20 1.472(2) . ?
N5 C22 1.385(2) . ?
N6 C26 1.392(2) . ?
N6 C30 1.345(2) . ?
N6 C31 1.459(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.513(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.504(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.413(2) . ?
C22 C27 1.387(2) . ?
C23 C24 1.355(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.406(2) . ?
C25 C26 1.404(2) . ?
C25 C28 1.449(2) . ?
C26 C27 1.407(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.424(3) . ?
C29 C30 1.371(3) . ?
C29 C34 1.493(2) . ?
C30 H30 0.9300 . ?
C31 H31 0.9800 . ?
C31 C32 1.489(3) . ?
C31 C33 1.497(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.498(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
O7 C35 1.234(3) . ?
O8 C35 1.242(2) . ?
O9 C42 1.231(3) . ?
O10 C42 1.287(3) . ?
C35 C36 1.518(3) . ?
C36 C37 1.394(2) . ?
C36 C41 1.371(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.392(3) . ?
C38 C39 1.375(3) . ?
C38 C42 1.508(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.390(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.372(4) . ?
C41 H41 0.9300 . ?
O11 H11A 0.8501 . ?
O11 H11B 0.8499 . ?
O11A H11C 0.8501 . ?
O11A H11D 0.8499 . ?
O12 H12A 0.8201 . ?
O12 H12B 0.8201 . ?
O13 H13A 0.8200 . ?
O13 H13B 0.8643 . ?

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
C17 O2 H2 109.5 . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 H1A 109.1 . . ?
C1 N1 H1B 109.1 . . ?
C4 N1 H1A 109.1 . . ?
C4 N1 H1B 109.1 . . ?
C4 N1 C1 112.47(16) . . ?
C2 N2 C3 111.68(16) . . ?
C5 N2 C2 122.14(15) . . ?
C5 N2 C3 119.78(15) . . ?
C7 N3 C14 119.67(14) . . ?
C13 N3 C7 119.64(15) . . ?
C13 N3 C14 120.44(15) . . ?
N1 C1 H1C 109.7 . . ?
N1 C1 H1D 109.7 . . ?
N1 C1 C2 110.00(18) . . ?
H1C C1 H1D 108.2 . . ?
C2 C1 H1C 109.7 . . ?
C2 C1 H1D 109.7 . . ?
N2 C2 C1 108.03(16) . . ?
N2 C2 H2A 110.1 . . ?
N2 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N2 C3 H3A 109.9 . . ?
N2 C3 H3B 109.9 . . ?
N2 C3 C4 109.01(18) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
N1 C4 C3 109.48(17) . . ?
N1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C6 122.91(16) . . ?
N2 C5 C10 119.55(16) . . ?
C6 C5 C10 117.32(16) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.23(16) . . ?
C7 C6 H6 119.9 . . ?
N3 C7 C6 120.53(15) . . ?
N3 C7 C8 118.65(15) . . ?
C6 C7 C8 120.81(16) . . ?
C7 C8 C9 118.36(15) . . ?
C7 C8 C11 121.79(16) . . ?
C9 C8 C11 119.84(16) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.00(16) . . ?
C10 C9 H9 120.0 . . ?
F1 C10 C5 117.82(17) . . ?
C9 C10 F1 119.02(17) . . ?
C9 C10 C5 123.09(17) . . ?
O1 C11 C8 121.49(17) . . ?
O1 C11 C12 122.85(16) . . ?
C12 C11 C8 115.65(16) . . ?
C11 C12 C17 122.26(17) . . ?
C13 C12 C11 120.23(16) . . ?
C13 C12 C17 117.51(18) . . ?
N3 C13 C12 124.00(17) . . ?
N3 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
N3 C14 H14 115.7 . . ?
N3 C14 C15 119.05(16) . . ?
N3 C14 C16 119.14(18) . . ?
C15 C14 H14 115.7 . . ?
C15 C14 C16 60.39(14) . . ?
C16 C14 H14 115.7 . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
C14 C15 C16 59.83(14) . . ?
H15A C15 H15B 114.9 . . ?
C16 C15 H15A 117.8 . . ?
C16 C15 H15B 117.8 . . ?
C14 C16 C15 59.78(14) . . ?
C14 C16 H16A 117.8 . . ?
C14 C16 H16B 117.8 . . ?
C15 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
H16A C16 H16B 114.9 . . ?
O2 C17 C12 115.29(19) . . ?
O3 C17 O2 121.22(19) . . ?
O3 C17 C12 123.5(2) . . ?
C34 O6 H6A 109.5 . . ?
H4C N4 H4D 108.0 . . ?
C18 N4 H4C 109.3 . . ?
C18 N4 H4D 109.3 . . ?
C18 N4 C21 111.45(15) . . ?
C21 N4 H4C 109.3 . . ?
C21 N4 H4D 109.3 . . ?
C19 N5 C20 111.22(15) . . ?
C22 N5 C19 119.07(14) . . ?
C22 N5 C20 120.40(15) . . ?
C26 N6 C31 119.65(13) . . ?
C30 N6 C26 120.26(14) . . ?
C30 N6 C31 119.99(14) . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 C19 110.92(17) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
N5 C19 C18 110.27(16) . . ?
N5 C19 H19A 109.6 . . ?
N5 C19 H19B 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
N5 C20 H20A 109.8 . . ?
N5 C20 H20B 109.8 . . ?
N5 C20 C21 109.57(17) . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
N4 C21 C20 108.73(17) . . ?
N4 C21 H21A 109.9 . . ?
N4 C21 H21B 109.9 . . ?
C20 C21 H21A 109.9 . . ?
C20 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
N5 C22 C23 120.28(15) . . ?
N5 C22 C27 123.08(15) . . ?
C27 C22 C23 116.39(15) . . ?
F2 C23 C22 119.04(15) . . ?
F2 C23 C24 117.55(16) . . ?
C24 C23 C22 123.36(15) . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.00(15) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C28 120.14(15) . . ?
C26 C25 C24 118.28(15) . . ?
C26 C25 C28 121.56(15) . . ?
N6 C26 C25 118.77(14) . . ?
N6 C26 C27 121.06(14) . . ?
C25 C26 C27 120.16(14) . . ?
C22 C27 C26 121.45(15) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
O4 C28 C25 120.91(16) . . ?
O4 C28 C29 123.45(16) . . ?
C29 C28 C25 115.64(15) . . ?
C28 C29 C34 120.45(17) . . ?
C30 C29 C28 120.38(15) . . ?
C30 C29 C34 119.18(17) . . ?
N6 C30 C29 123.36(16) . . ?
N6 C30 H30 118.3 . . ?
C29 C30 H30 118.3 . . ?
N6 C31 H31 116.0 . . ?
N6 C31 C32 118.37(16) . . ?
N6 C31 C33 118.82(15) . . ?
C32 C31 H31 116.0 . . ?
C32 C31 C33 60.24(14) . . ?
C33 C31 H31 116.0 . . ?
C31 C32 H32A 117.8 . . ?
C31 C32 H32B 117.8 . . ?
C31 C32 C33 60.15(13) . . ?
H32A C32 H32B 114.9 . . ?
C33 C32 H32A 117.8 . . ?
C33 C32 H32B 117.8 . . ?
C31 C33 C32 59.62(13) . . ?
C31 C33 H33A 117.8 . . ?
C31 C33 H33B 117.8 . . ?
C32 C33 H33A 117.8 . . ?
C32 C33 H33B 117.8 . . ?
H33A C33 H33B 114.9 . . ?
O5 C34 O6 121.55(19) . . ?
O5 C34 C29 122.9(2) . . ?
O6 C34 C29 115.54(18) . . ?
O7 C35 O8 125.2(2) . . ?
O7 C35 C36 118.33(17) . . ?
O8 C35 C36 116.4(2) . . ?
C37 C36 C35 119.67(18) . . ?
C41 C36 C35 120.29(18) . . ?
C41 C36 C37 120.04(19) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.06(18) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C42 118.96(18) . . ?
C39 C38 C37 119.07(18) . . ?
C39 C38 C42 121.96(18) . . ?
C38 C39 H39 119.7 . . ?
C38 C39 C40 120.5(2) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.9 . . ?
C41 C40 C39 120.2(2) . . ?
C41 C40 H40 119.9 . . ?
C36 C41 C40 120.1(2) . . ?
C36 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
O9 C42 O10 124.17(19) . . ?
O9 C42 C38 119.86(18) . . ?
O10 C42 C38 116.0(2) . . ?
H11A O11 H11B 104.5 . . ?
H11C O11A H11D 104.5 . . ?
H12A O12 H12B 121.3 . . ?
H13A O13 H13B 108.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82 1.80 2.558(2) 153.7 . yes
N1 H1A O10 0.89 1.98 2.848(3) 163.9 . yes
N1 H1B O8 0.89 1.85 2.635(2) 146.6 1_455 yes
O6 H6A O4 0.82 1.75 2.517(2) 154.6 . yes
N4 H4C O12 0.89 1.96 2.831(3) 165.1 2_666 yes
N4 H4D O10 0.89 1.96 2.815(2) 161.0 1_556 yes
C20 H20A F2 0.97 2.17 2.837(3) 124.5 . yes
O11 H11A O9 0.85 1.97 2.817(4) 179.1 2_665 yes
O11A H11C O9 0.85 1.96 2.808(16) 173.9 2_665 yes
O12 H12A O7 0.82 2.06 2.877(3) 174.2 2_765 yes
O12 H12B O7 0.82 2.08 2.840(3) 153.2 1_455 yes
O13 H13A O10 0.82 1.91 2.662(5) 151.3 . yes
O13 H13B O10 0.86 1.96 2.774(5) 155.6 2_675 yes

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 C11 C12 C13 179.82(16) . . . . ?
O1 C11 C12 C17 0.3(3) . . . . ?
N1 C1 C2 N2 57.1(2) . . . . ?
N2 C3 C4 N1 -57.0(3) . . . . ?
N2 C5 C6 C7 -177.87(16) . . . . ?
N2 C5 C10 F1 2.8(3) . . . . ?
N2 C5 C10 C9 179.86(18) . . . . ?
N3 C7 C8 C9 -178.55(15) . . . . ?
N3 C7 C8 C11 -0.1(2) . . . . ?
N3 C14 C15 C16 109.0(2) . . . . ?
N3 C14 C16 C15 -108.8(2) . . . . ?
C1 N1 C4 C3 54.6(3) . . . . ?
C2 N2 C3 C4 63.3(2) . . . . ?
C2 N2 C5 C6 16.5(3) . . . . ?
C2 N2 C5 C10 -157.93(18) . . . . ?
C3 N2 C2 C1 -62.8(2) . . . . ?
C3 N2 C5 C6 -133.1(2) . . . . ?
C3 N2 C5 C10 52.5(3) . . . . ?
C4 N1 C1 C2 -54.9(2) . . . . ?
C5 N2 C2 C1 145.49(19) . . . . ?
C5 N2 C3 C4 -144.20(19) . . . . ?
C5 C6 C7 N3 -179.20(15) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C5 C10 F1 -171.88(17) . . . . ?
C6 C5 C10 C9 5.2(3) . . . . ?
C6 C7 C8 C9 2.6(2) . . . . ?
C6 C7 C8 C11 -178.96(16) . . . . ?
C7 N3 C13 C12 -2.4(3) . . . . ?
C7 N3 C14 C15 76.2(2) . . . . ?
C7 N3 C14 C16 146.45(18) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C11 O1 179.37(16) . . . . ?
C7 C8 C11 C12 -0.4(2) . . . . ?
C8 C9 C10 F1 174.00(17) . . . . ?
C8 C9 C10 C5 -3.0(3) . . . . ?
C8 C11 C12 C13 -0.4(2) . . . . ?
C8 C11 C12 C17 -179.85(15) . . . . ?
C9 C8 C11 O1 -2.2(3) . . . . ?
C9 C8 C11 C12 177.97(16) . . . . ?
C10 C5 C6 C7 -3.4(3) . . . . ?
C11 C8 C9 C10 -179.43(17) . . . . ?
C11 C12 C13 N3 1.9(3) . . . . ?
C11 C12 C17 O2 -2.5(3) . . . . ?
C11 C12 C17 O3 177.86(19) . . . . ?
C13 N3 C7 C6 -179.64(15) . . . . ?
C13 N3 C7 C8 1.5(2) . . . . ?
C13 N3 C14 C15 -109.7(2) . . . . ?
C13 N3 C14 C16 -39.4(3) . . . . ?
C13 C12 C17 O2 178.02(16) . . . . ?
C13 C12 C17 O3 -1.6(3) . . . . ?
C14 N3 C7 C6 -5.5(2) . . . . ?
C14 N3 C7 C8 175.70(15) . . . . ?
C14 N3 C13 C12 -176.59(16) . . . . ?
C17 C12 C13 N3 -178.64(16) . . . . ?
F2 C23 C24 C25 -171.75(16) . . . . ?
O4 C28 C29 C30 179.79(16) . . . . ?
O4 C28 C29 C34 0.1(3) . . . . ?
N4 C18 C19 N5 -54.5(2) . . . . ?
N5 C20 C21 N4 59.7(2) . . . . ?
N5 C22 C23 F2 -2.2(3) . . . . ?
N5 C22 C23 C24 -179.67(17) . . . . ?
N5 C22 C27 C26 174.37(15) . . . . ?
N6 C26 C27 C22 -176.77(15) . . . . ?
N6 C31 C32 C33 -108.81(18) . . . . ?
N6 C31 C33 C32 108.06(19) . . . . ?
C18 N4 C21 C20 -57.4(2) . . . . ?
C19 N5 C20 C21 -61.4(2) . . . . ?
C19 N5 C22 C23 167.18(17) . . . . ?
C19 N5 C22 C27 -6.9(3) . . . . ?
C20 N5 C19 C18 58.1(2) . . . . ?
C20 N5 C22 C23 -49.1(2) . . . . ?
C20 N5 C22 C27 136.85(19) . . . . ?
C21 N4 C18 C19 55.0(2) . . . . ?
C22 N5 C19 C18 -155.13(17) . . . . ?
C22 N5 C20 C21 152.33(18) . . . . ?
C22 C23 C24 C25 5.7(3) . . . . ?
C23 C22 C27 C26 0.1(3) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C23 C24 C25 C28 177.86(16) . . . . ?
C24 C25 C26 N6 177.20(14) . . . . ?
C24 C25 C26 C27 -3.9(2) . . . . ?
C24 C25 C28 O4 2.2(2) . . . . ?
C24 C25 C28 C29 -178.00(15) . . . . ?
C25 C26 C27 C22 4.4(3) . . . . ?
C25 C28 C29 C30 0.0(2) . . . . ?
C25 C28 C29 C34 -179.72(15) . . . . ?
C26 N6 C30 C29 -0.9(3) . . . . ?
C26 N6 C31 C32 137.73(18) . . . . ?
C26 N6 C31 C33 68.0(2) . . . . ?
C26 C25 C28 O4 -179.01(15) . . . . ?
C26 C25 C28 C29 0.8(2) . . . . ?
C27 C22 C23 F2 172.22(16) . . . . ?
C27 C22 C23 C24 -5.2(3) . . . . ?
C28 C25 C26 N6 -1.6(2) . . . . ?
C28 C25 C26 C27 177.28(15) . . . . ?
C28 C29 C30 N6 0.1(3) . . . . ?
C28 C29 C34 O5 -178.6(2) . . . . ?
C28 C29 C34 O6 0.7(3) . . . . ?
C30 N6 C26 C25 1.7(2) . . . . ?
C30 N6 C26 C27 -177.23(15) . . . . ?
C30 N6 C31 C32 -45.7(2) . . . . ?
C30 N6 C31 C33 -115.44(19) . . . . ?
C30 C29 C34 O5 1.7(3) . . . . ?
C30 C29 C34 O6 -179.01(17) . . . . ?
C31 N6 C26 C25 178.20(15) . . . . ?
C31 N6 C26 C27 -0.7(2) . . . . ?
C31 N6 C30 C29 -177.44(17) . . . . ?
C34 C29 C30 N6 179.79(17) . . . . ?
O7 C35 C36 C37 -28.0(3) . . . . ?
O7 C35 C36 C41 152.4(2) . . . . ?
O8 C35 C36 C37 153.4(2) . . . . ?
O8 C35 C36 C41 -26.2(3) . . . . ?
C35 C36 C37 C38 178.48(16) . . . . ?
C35 C36 C41 C40 -177.7(2) . . . . ?
C36 C37 C38 C39 0.4(3) . . . . ?
C36 C37 C38 C42 -178.29(16) . . . . ?
C37 C36 C41 C40 2.7(4) . . . . ?
C37 C38 C39 C40 0.2(4) . . . . ?
C37 C38 C42 O9 -19.5(3) . . . . ?
C37 C38 C42 O10 159.42(18) . . . . ?
C38 C39 C40 C41 0.6(5) . . . . ?
C39 C38 C42 O9 161.8(2) . . . . ?
C39 C38 C42 O10 -19.3(3) . . . . ?
C39 C40 C41 C36 -2.1(5) . . . . ?
C41 C36 C37 C38 -1.9(3) . . . . ?
C42 C38 C39 C40 178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
