# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_IOD1038_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1843977'
_audit_update_record             
;
2018-05-18 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 F N4 O5'
_chemical_formula_weight         564.56

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'

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

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

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

_cell_length_a                   7.7342(5)
_cell_length_b                   11.9996(8)
_cell_length_c                   14.6465(10)
_cell_angle_alpha                97.469(2)
_cell_angle_beta                 92.265(2)
_cell_angle_gamma                91.035(2)
_cell_volume                     1346.35(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.199
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41972
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         27.188
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5937
_reflns_number_gt                4857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.5682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0159(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5937
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49807(18) 0.63664(10) 0.57296(8) 0.0509(3) Uani 1 1 d . . . . .
O4 O 0.83661(19) 0.71390(11) 0.90732(8) 0.0547(3) Uani 1 1 d . . . . .
F1 F 0.6420(2) 0.34203(12) 0.95946(9) 0.0890(5) Uani 1 1 d . . . . .
N2 N 0.93845(19) 0.57472(12) 0.64977(9) 0.0419(3) Uani 1 1 d . . . . .
H2 H 0.9343 0.5385 0.5950 0.050 Uiso 1 1 calc R U . . .
N4 N 0.5531(2) 0.46312(11) 0.61552(9) 0.0441(3) Uani 1 1 d . . . . .
H4 H 0.5419 0.4240 0.5620 0.053 Uiso 1 1 calc R U . . .
O3 O 1.2322(2) 0.28676(12) 0.61430(11) 0.0671(4) Uani 1 1 d . . . . .
N3 N 0.44827(19) 0.68240(11) 0.77913(10) 0.0430(3) Uani 1 1 d . . . . .
H3 H 0.3691 0.6585 0.8119 0.052 Uiso 1 1 calc R U . . .
O5 O 0.8917(2) 1.16146(14) 0.56349(12) 0.0758(5) Uani 1 1 d . . . . .
O2 O 1.0858(2) 0.40756(14) 0.55149(9) 0.0754(5) Uani 1 1 d . . . . .
N1 N 1.1445(2) 0.37053(13) 0.62016(11) 0.0499(4) Uani 1 1 d . . . . .
C25 C 0.8587(2) 0.66938(13) 0.82974(10) 0.0371(3) Uani 1 1 d . . . . .
C24 C 0.7479(2) 0.69760(12) 0.74644(10) 0.0340(3) Uani 1 1 d . . . . .
C31 C 1.0101(2) 0.52743(14) 0.71981(10) 0.0366(3) Uani 1 1 d . . . . .
C26 C 0.9850(2) 0.57833(14) 0.81151(10) 0.0381(3) Uani 1 1 d . . . . .
C16 C 0.6693(2) 0.81673(13) 0.76591(10) 0.0376(3) Uani 1 1 d . . . . .
H16 H 0.7006 0.8455 0.8303 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5987(2) 0.50323(13) 0.77091(11) 0.0372(3) Uani 1 1 d . . . . .
C7 C 0.5390(2) 0.57554(13) 0.63070(10) 0.0392(4) Uani 1 1 d . . . . .
C17 C 0.7322(2) 0.90362(13) 0.70791(11) 0.0403(4) Uani 1 1 d . . . . .
C4 C 0.5882(2) 0.41731(13) 0.69768(11) 0.0402(4) Uani 1 1 d . . . . .
C9 C 0.4701(2) 0.79726(13) 0.75928(11) 0.0396(4) Uani 1 1 d . . . . .
H9 H 0.4273 0.8020 0.6961 0.048 Uiso 1 1 calc R U . . .
C32 C 0.8682(2) 0.68597(14) 0.66555(10) 0.0394(4) Uani 1 1 d . . . . .
H32A H 0.8046 0.7014 0.6103 0.047 Uiso 1 1 calc R U . . .
H32B H 0.9624 0.7410 0.6781 0.047 Uiso 1 1 calc R U . . .
C8 C 0.5820(2) 0.61483(12) 0.73465(10) 0.0355(3) Uani 1 1 d . . . . .
C30 C 1.1094(2) 0.42910(15) 0.71014(11) 0.0420(4) Uani 1 1 d . . . . .
C10 C 0.3773(2) 0.88133(14) 0.82500(12) 0.0452(4) Uani 1 1 d . . . . .
C23 C 0.6778(3) 0.90331(15) 0.61650(12) 0.0488(4) Uani 1 1 d . . . . .
H23 H 0.6041 0.8456 0.5887 0.059 Uiso 1 1 calc R U . . .
C27 C 1.0616(2) 0.53412(17) 0.88515(12) 0.0494(4) Uani 1 1 d . . . . .
H27 H 1.0475 0.5699 0.9445 0.059 Uiso 1 1 calc R U . . .
C6 C 0.6142(2) 0.47917(15) 0.86010(12) 0.0456(4) Uani 1 1 d . . . . .
H6 H 0.6158 0.5355 0.9102 0.055 Uiso 1 1 calc R U . . .
C18 C 0.8460(3) 0.98941(15) 0.74591(13) 0.0496(4) Uani 1 1 d . . . . .
H18 H 0.8876 0.9909 0.8065 0.059 Uiso 1 1 calc R U . . .
C20 C 0.8383(3) 1.07249(16) 0.60595(14) 0.0524(5) Uani 1 1 d . . . . .
C3 C 0.6030(3) 0.30640(15) 0.71058(14) 0.0531(5) Uani 1 1 d . . . . .
H3A H 0.5989 0.2496 0.6608 0.064 Uiso 1 1 calc R U . . .
C22 C 0.7300(3) 0.98636(17) 0.56534(13) 0.0536(5) Uani 1 1 d . . . . .
H22 H 0.6920 0.9839 0.5040 0.064 Uiso 1 1 calc R U . . .
C1 C 0.6272(3) 0.36770(17) 0.87157(14) 0.0560(5) Uani 1 1 d . . . . .
C29 C 1.1802(2) 0.38575(17) 0.78574(13) 0.0530(5) Uani 1 1 d . . . . .
H29 H 1.2433 0.3202 0.7772 0.064 Uiso 1 1 calc R U . . .
C28 C 1.1584(3) 0.4384(2) 0.87320(13) 0.0596(5) Uani 1 1 d . . . . .
H28 H 1.2083 0.4098 0.9239 0.071 Uiso 1 1 calc R U . . .
C19 C 0.8987(3) 1.07253(17) 0.69560(15) 0.0590(5) Uani 1 1 d . . . . .
H19 H 0.9755 1.1290 0.7225 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6243(3) 0.28190(16) 0.80030(16) 0.0607(5) Uani 1 1 d . . . . .
H2A H 0.6366 0.2080 0.8118 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3472(4) 0.98684(19) 0.80250(19) 0.0753(7) Uani 1 1 d . . . . .
H11 H 0.3762 1.0045 0.7450 0.090 Uiso 1 1 calc R U . . .
C21 C 0.8298(4) 1.1672(2) 0.47244(18) 0.0814(7) Uani 1 1 d . . . . .
H21A H 0.8663 1.1025 0.4329 0.122 Uiso 1 1 calc R U . . .
H21B H 0.8753 1.2341 0.4518 0.122 Uiso 1 1 calc R U . . .
H21C H 0.7057 1.1689 0.4706 0.122 Uiso 1 1 calc R U . . .
C12 C 0.2737(4) 1.0679(2) 0.8651(2) 0.0894(9) Uani 1 1 d . . . . .
H12 H 0.2572 1.1399 0.8497 0.107 Uiso 1 1 calc R U . . .
C13 C 0.2259(4) 1.0430(2) 0.9482(2) 0.0930(9) Uani 1 1 d . . . . .
H13 H 0.1772 1.0969 0.9903 0.112 Uiso 1 1 calc R U . . .
C15 C 0.3248(5) 0.8581(2) 0.90699(19) 0.1167(14) Uani 1 1 d . . . . .
H15 H 0.3388 0.7862 0.9230 0.140 Uiso 1 1 calc R U . . .
C14 C 0.2504(7) 0.9392(3) 0.9680(2) 0.151(2) Uani 1 1 d . . . . .
H14 H 0.2165 0.9206 1.0244 0.181 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2254(19) . ?
O4 C25 1.2110(18) . ?
F1 C1 1.363(2) . ?
N2 C31 1.341(2) . ?
N2 C32 1.444(2) . ?
N2 H2 0.8600 . ?
N4 C7 1.345(2) . ?
N4 C4 1.406(2) . ?
N4 H4 0.8600 . ?
O3 N1 1.219(2) . ?
N3 C8 1.448(2) . ?
N3 C9 1.453(2) . ?
N3 H3 0.8600 . ?
O5 C20 1.369(2) . ?
O5 C21 1.410(3) . ?
O2 N1 1.226(2) . ?
N1 C30 1.449(2) . ?
C25 C26 1.484(2) . ?
C25 C24 1.540(2) . ?
C24 C32 1.529(2) . ?
C24 C16 1.560(2) . ?
C24 C8 1.598(2) . ?
C31 C30 1.414(2) . ?
C31 C26 1.423(2) . ?
C26 C27 1.380(2) . ?
C16 C17 1.513(2) . ?
C16 C9 1.552(2) . ?
C16 H16 0.9800 . ?
C5 C6 1.375(2) . ?
C5 C4 1.387(2) . ?
C5 C8 1.509(2) . ?
C7 C8 1.555(2) . ?
C17 C23 1.387(2) . ?
C17 C18 1.387(2) . ?
C4 C3 1.374(2) . ?
C9 C10 1.512(2) . ?
C9 H9 0.9800 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C30 C29 1.381(2) . ?
C10 C15 1.344(3) . ?
C10 C11 1.371(3) . ?
C23 C22 1.386(3) . ?
C23 H23 0.9300 . ?
C27 C28 1.378(3) . ?
C27 H27 0.9300 . ?
C6 C1 1.375(3) . ?
C6 H6 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C20 C19 1.376(3) . ?
C20 C22 1.376(3) . ?
C3 C2 1.388(3) . ?
C3 H3A 0.9300 . ?
C22 H22 0.9300 . ?
C1 C2 1.367(3) . ?
C29 C28 1.371(3) . ?
C29 H29 0.9300 . ?
C28 H28 0.9300 . ?
C19 H19 0.9300 . ?
C2 H2A 0.9300 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C12 C13 1.354(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.330(4) . ?
C13 H13 0.9300 . ?
C15 C14 1.382(4) . ?
C15 H15 0.9300 . ?
C14 H14 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
C31 N2 C32 120.53(13) . . ?
C31 N2 H2 119.7 . . ?
C32 N2 H2 119.7 . . ?
C7 N4 C4 111.84(13) . . ?
C7 N4 H4 124.1 . . ?
C4 N4 H4 124.1 . . ?
C8 N3 C9 108.70(13) . . ?
C8 N3 H3 125.7 . . ?
C9 N3 H3 125.7 . . ?
C20 O5 C21 118.30(19) . . ?
O3 N1 O2 121.62(16) . . ?
O3 N1 C30 119.64(16) . . ?
O2 N1 C30 118.74(15) . . ?
O4 C25 C26 121.25(15) . . ?
O4 C25 C24 121.87(15) . . ?
C26 C25 C24 116.72(12) . . ?
C32 C24 C25 105.46(13) . . ?
C32 C24 C16 113.26(12) . . ?
C25 C24 C16 111.41(12) . . ?
C32 C24 C8 115.37(12) . . ?
C25 C24 C8 107.71(12) . . ?
C16 C24 C8 103.63(12) . . ?
N2 C31 C30 125.01(14) . . ?
N2 C31 C26 118.53(14) . . ?
C30 C31 C26 116.45(14) . . ?
C27 C26 C31 120.10(16) . . ?
C27 C26 C25 118.93(14) . . ?
C31 C26 C25 120.48(14) . . ?
C17 C16 C9 113.64(13) . . ?
C17 C16 C24 116.29(13) . . ?
C9 C16 C24 105.67(12) . . ?
C17 C16 H16 106.9 . . ?
C9 C16 H16 106.9 . . ?
C24 C16 H16 106.9 . . ?
C6 C5 C4 120.48(15) . . ?
C6 C5 C8 130.12(14) . . ?
C4 C5 C8 109.33(13) . . ?
O1 C7 N4 126.07(14) . . ?
O1 C7 C8 125.70(14) . . ?
N4 C7 C8 108.23(13) . . ?
C23 C17 C18 117.09(16) . . ?
C23 C17 C16 122.57(15) . . ?
C18 C17 C16 120.33(15) . . ?
C3 C4 C5 121.85(16) . . ?
C3 C4 N4 128.85(16) . . ?
C5 C4 N4 109.22(14) . . ?
N3 C9 C10 112.90(14) . . ?
N3 C9 C16 103.40(13) . . ?
C10 C9 C16 112.54(14) . . ?
N3 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C16 C9 H9 109.3 . . ?
N2 C32 C24 111.61(13) . . ?
N2 C32 H32A 109.3 . . ?
C24 C32 H32A 109.3 . . ?
N2 C32 H32B 109.3 . . ?
C24 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
N3 C8 C5 112.15(13) . . ?
N3 C8 C7 113.22(13) . . ?
C5 C8 C7 100.92(12) . . ?
N3 C8 C24 103.44(12) . . ?
C5 C8 C24 117.40(13) . . ?
C7 C8 C24 110.10(12) . . ?
C29 C30 C31 121.69(16) . . ?
C29 C30 N1 116.95(16) . . ?
C31 C30 N1 121.35(15) . . ?
C15 C10 C11 117.5(2) . . ?
C15 C10 C9 122.63(18) . . ?
C11 C10 C9 119.85(18) . . ?
C22 C23 C17 122.04(17) . . ?
C22 C23 H23 119.0 . . ?
C17 C23 H23 119.0 . . ?
C28 C27 C26 121.87(17) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C1 C6 C5 116.67(17) . . ?
C1 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C19 C18 C17 121.33(18) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
O5 C20 C19 115.97(18) . . ?
O5 C20 C22 124.50(19) . . ?
C19 C20 C22 119.53(17) . . ?
C4 C3 C2 117.83(17) . . ?
C4 C3 H3A 121.1 . . ?
C2 C3 H3A 121.1 . . ?
C20 C22 C23 119.47(18) . . ?
C20 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
F1 C1 C2 118.56(18) . . ?
F1 C1 C6 117.60(18) . . ?
C2 C1 C6 123.84(18) . . ?
C28 C29 C30 120.64(18) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C28 C27 119.19(17) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C20 C19 C18 120.48(18) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C1 C2 C3 119.21(17) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C10 C15 C14 121.1(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C25 C24 C32 147.31(16) . . . . ?
C26 C25 C24 C32 -37.36(18) . . . . ?
O4 C25 C24 C16 24.0(2) . . . . ?
C26 C25 C24 C16 -160.63(13) . . . . ?
O4 C25 C24 C8 -88.98(18) . . . . ?
C26 C25 C24 C8 86.36(16) . . . . ?
C32 N2 C31 C30 -167.99(16) . . . . ?
C32 N2 C31 C26 12.4(2) . . . . ?
N2 C31 C26 C27 -177.84(16) . . . . ?
C30 C31 C26 C27 2.5(2) . . . . ?
N2 C31 C26 C25 10.3(2) . . . . ?
C30 C31 C26 C25 -169.35(15) . . . . ?
O4 C25 C26 C27 8.4(3) . . . . ?
C24 C25 C26 C27 -166.92(15) . . . . ?
O4 C25 C26 C31 -179.61(16) . . . . ?
C24 C25 C26 C31 5.0(2) . . . . ?
C32 C24 C16 C17 -4.2(2) . . . . ?
C25 C24 C16 C17 114.49(15) . . . . ?
C8 C24 C16 C17 -129.95(14) . . . . ?
C32 C24 C16 C9 122.88(14) . . . . ?
C25 C24 C16 C9 -118.41(13) . . . . ?
C8 C24 C16 C9 -2.86(14) . . . . ?
C4 N4 C7 O1 -174.98(17) . . . . ?
C4 N4 C7 C8 4.44(19) . . . . ?
C9 C16 C17 C23 -47.7(2) . . . . ?
C24 C16 C17 C23 75.3(2) . . . . ?
C9 C16 C17 C18 130.95(17) . . . . ?
C24 C16 C17 C18 -106.02(18) . . . . ?
C6 C5 C4 C3 -3.9(3) . . . . ?
C8 C5 C4 C3 178.63(17) . . . . ?
C6 C5 C4 N4 173.20(15) . . . . ?
C8 C5 C4 N4 -4.25(19) . . . . ?
C7 N4 C4 C3 176.63(19) . . . . ?
C7 N4 C4 C5 -0.2(2) . . . . ?
C8 N3 C9 C10 -161.66(14) . . . . ?
C8 N3 C9 C16 -39.76(16) . . . . ?
C17 C16 C9 N3 153.20(13) . . . . ?
C24 C16 C9 N3 24.52(15) . . . . ?
C17 C16 C9 C10 -84.66(17) . . . . ?
C24 C16 C9 C10 146.67(13) . . . . ?
C31 N2 C32 C24 -49.1(2) . . . . ?
C25 C24 C32 N2 57.85(17) . . . . ?
C16 C24 C32 N2 179.93(13) . . . . ?
C8 C24 C32 N2 -60.87(18) . . . . ?
C9 N3 C8 C5 165.18(13) . . . . ?
C9 N3 C8 C7 -81.42(16) . . . . ?
C9 N3 C8 C24 37.72(15) . . . . ?
C6 C5 C8 N3 -50.0(2) . . . . ?
C4 C5 C8 N3 127.14(15) . . . . ?
C6 C5 C8 C7 -170.79(17) . . . . ?
C4 C5 C8 C7 6.34(17) . . . . ?
C6 C5 C8 C24 69.6(2) . . . . ?
C4 C5 C8 C24 -113.27(15) . . . . ?
O1 C7 C8 N3 52.9(2) . . . . ?
N4 C7 C8 N3 -126.48(15) . . . . ?
O1 C7 C8 C5 172.97(17) . . . . ?
N4 C7 C8 C5 -6.45(17) . . . . ?
O1 C7 C8 C24 -62.3(2) . . . . ?
N4 C7 C8 C24 118.29(15) . . . . ?
C32 C24 C8 N3 -144.22(13) . . . . ?
C25 C24 C8 N3 98.32(13) . . . . ?
C16 C24 C8 N3 -19.84(14) . . . . ?
C32 C24 C8 C5 91.69(16) . . . . ?
C25 C24 C8 C5 -25.77(17) . . . . ?
C16 C24 C8 C5 -143.93(13) . . . . ?
C32 C24 C8 C7 -22.95(18) . . . . ?
C25 C24 C8 C7 -140.42(13) . . . . ?
C16 C24 C8 C7 101.43(13) . . . . ?
N2 C31 C30 C29 179.53(17) . . . . ?
C26 C31 C30 C29 -0.8(2) . . . . ?
N2 C31 C30 N1 0.8(3) . . . . ?
C26 C31 C30 N1 -179.56(15) . . . . ?
O3 N1 C30 C29 0.4(3) . . . . ?
O2 N1 C30 C29 -178.98(18) . . . . ?
O3 N1 C30 C31 179.17(17) . . . . ?
O2 N1 C30 C31 -0.2(3) . . . . ?
N3 C9 C10 C15 18.2(3) . . . . ?
C16 C9 C10 C15 -98.4(3) . . . . ?
N3 C9 C10 C11 -163.27(19) . . . . ?
C16 C9 C10 C11 80.1(2) . . . . ?
C18 C17 C23 C22 -1.8(3) . . . . ?
C16 C17 C23 C22 176.91(17) . . . . ?
C31 C26 C27 C28 -2.3(3) . . . . ?
C25 C26 C27 C28 169.63(18) . . . . ?
C4 C5 C6 C1 3.1(3) . . . . ?
C8 C5 C6 C1 179.99(18) . . . . ?
C23 C17 C18 C19 1.8(3) . . . . ?
C16 C17 C18 C19 -176.94(18) . . . . ?
C21 O5 C20 C19 -178.3(2) . . . . ?
C21 O5 C20 C22 1.2(3) . . . . ?
C5 C4 C3 C2 1.8(3) . . . . ?
N4 C4 C3 C2 -174.74(18) . . . . ?
O5 C20 C22 C23 -176.90(19) . . . . ?
C19 C20 C22 C23 2.5(3) . . . . ?
C17 C23 C22 C20 -0.3(3) . . . . ?
C5 C6 C1 F1 -179.75(17) . . . . ?
C5 C6 C1 C2 -0.4(3) . . . . ?
C31 C30 C29 C28 -1.1(3) . . . . ?
N1 C30 C29 C28 177.69(18) . . . . ?
C30 C29 C28 C27 1.4(3) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
O5 C20 C19 C18 176.93(19) . . . . ?
C22 C20 C19 C18 -2.5(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
F1 C1 C2 C3 177.68(19) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C4 C3 C2 C1 0.9(3) . . . . ?
C15 C10 C11 C12 3.5(4) . . . . ?
C9 C10 C11 C12 -175.2(2) . . . . ?
C10 C11 C12 C13 -2.0(5) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C11 C10 C15 C14 -2.8(6) . . . . ?
C9 C10 C15 C14 175.8(4) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C10 C15 C14 C13 0.6(8) . . . . ?

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
C32 H32A O1 0.97 2.50 3.132(2) 122.8 .
C9 H9 O1 0.98 2.58 3.1469(19) 116.6 .
C16 H16 O4 0.98 2.30 2.828(2) 112.6 .
N4 H4 O1 0.86 2.03 2.8719(17) 167.9 2_666
N2 H2 O2 0.86 2.32 2.9816(19) 133.8 2_766
N2 H2 O2 0.86 2.03 2.6183(19) 125.0 .
N2 H2 O2 0.86 2.03 2.6183(19) 125.0 .
N2 H2 O2 0.86 2.32 2.9816(19) 133.8 2_766
N4 H4 O1 0.86 2.03 2.8719(17) 167.9 2_666
C16 H16 O4 0.98 2.30 2.828(2) 112.6 .
C9 H9 O1 0.98 2.58 3.1469(19) 116.6 .
C32 H32A O1 0.97 2.50 3.132(2) 122.8 .

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.040

