# Supplementary Information (SI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MAB_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127603'
loop_
_audit_author_name
_audit_author_address
'Dr. Thangavel Vijayakanth'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2025-04-02 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            'C23 H14 F6 N2 O'
_chemical_formula_weight         448.36

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'

_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                   7.6045(15)
_cell_length_b                   9.8170(19)
_cell_length_c                   14.024(3)
_cell_angle_alpha                76.190(6)
_cell_angle_beta                 74.705(6)
_cell_angle_gamma                74.570(6)
_cell_volume                     957.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3465
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14347
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.531
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4748
_reflns_number_gt                3512
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0594P)²+0.4785P] 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       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4748
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
F3 F 0.94618(17) 0.22057(15) 0.92416(9) 0.0335(3) Uani 1 1 d . . . . .
F5 F 1.09396(18) -0.01419(14) 0.26328(10) 0.0343(3) Uani 1 1 d . . . . .
F4 F 1.0514(2) -0.20220(14) 0.37334(10) 0.0379(3) Uani 1 1 d . . . . .
O1 O 0.23977(19) 0.39073(15) 0.49423(10) 0.0211(3) Uani 1 1 d . . . . .
F6 F 0.8722(2) -0.11423(17) 0.26840(11) 0.0431(4) Uani 1 1 d . . . . .
F1 F 0.7414(2) 0.2072(2) 1.05848(10) 0.0637(6) Uani 1 1 d . . . . .
N1 N 0.0108(2) 0.53779(16) 0.63749(11) 0.0151(3) Uani 1 1 d . . . . .
H1 H -0.0329 0.5490 0.5833 0.018 Uiso 1 1 calc R U . . .
N2 N 0.4583(2) 0.28403(17) 0.58813(11) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.4919 0.2820 0.6440 0.022 Uiso 1 1 calc R U . . .
F2 F 0.8263(3) 0.03598(15) 0.97598(17) 0.0746(7) Uani 1 1 d . . . . .
C6 C -0.0755(3) 0.60611(18) 0.71712(13) 0.0146(4) Uani 1 1 d . . . . .
C16 C 0.2927(3) 0.37281(19) 0.57286(13) 0.0153(4) Uani 1 1 d . . . . .
C5 C 0.0414(3) 0.55965(18) 0.78775(13) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.1775(3) 0.44833(19) 0.65520(13) 0.0150(4) Uani 1 1 d . . . . .
C13 C 0.6364(3) 0.2480(2) 0.90810(13) 0.0164(4) Uani 1 1 d . . . . .
C15 C 0.3979(3) 0.23343(19) 0.82956(13) 0.0160(4) Uani 1 1 d . . . . .
H15 H 0.3300 0.1772 0.8128 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3550(3) 0.38295(19) 0.80151(12) 0.0142(4) Uani 1 1 d . . . . .
C18 C 0.5806(3) 0.1949(2) 0.52130(13) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.2009(3) 0.45806(18) 0.74806(13) 0.0143(4) Uani 1 1 d . . . . .
C14 C 0.5398(3) 0.16608(19) 0.88202(13) 0.0163(4) Uani 1 1 d . . . . .
H14 H 0.5700 0.0643 0.8998 0.020 Uiso 1 1 calc R U . . .
C17 C 0.6237(3) 0.2452(2) 0.41796(14) 0.0196(4) Uani 1 1 d . . . . .
H17 H 0.5688 0.3404 0.3904 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5934(3) 0.3969(2) 0.88242(14) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.6593 0.4528 0.9010 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4532(3) 0.4637(2) 0.82933(14) 0.0181(4) Uani 1 1 d . . . . .
H10 H 0.4238 0.5655 0.8117 0.022 Uiso 1 1 calc R U . . .
C1 C -0.2461(3) 0.70507(19) 0.73357(14) 0.0168(4) Uani 1 1 d . . . . .
H1A H -0.3229 0.7352 0.6855 0.020 Uiso 1 1 calc R U . . .
C4 C -0.0160(3) 0.6152(2) 0.87771(13) 0.0180(4) Uani 1 1 d . . . . .
H4 H 0.0595 0.5858 0.9264 0.022 Uiso 1 1 calc R U . . .
C2 C -0.2980(3) 0.7568(2) 0.82197(14) 0.0197(4) Uani 1 1 d . . . . .
H2A H -0.4135 0.8238 0.8353 0.024 Uiso 1 1 calc R U . . .
C22 C 0.7477(3) 0.1549(2) 0.35577(14) 0.0205(4) Uani 1 1 d . . . . .
H22 H 0.7765 0.1881 0.2852 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6638(3) 0.0552(2) 0.56128(14) 0.0196(4) Uani 1 1 d . . . . .
H19 H 0.6343 0.0211 0.6317 0.024 Uiso 1 1 calc R U . . .
C3 C -0.1841(3) 0.7131(2) 0.89357(14) 0.0202(4) Uani 1 1 d . . . . .
H3 H -0.2240 0.7517 0.9537 0.024 Uiso 1 1 calc R U . . .
C21 C 0.8301(3) 0.0158(2) 0.39627(14) 0.0192(4) Uani 1 1 d . . . . .
C12 C 0.7880(3) 0.1767(2) 0.96565(15) 0.0228(4) Uani 1 1 d . . . . .
C20 C 0.7903(3) -0.0347(2) 0.49835(14) 0.0211(4) Uani 1 1 d . . . . .
H20 H 0.8479 -0.1293 0.5256 0.025 Uiso 1 1 calc R U . . .
C23 C 0.9611(3) -0.0777(2) 0.32643(15) 0.0241(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
F3 C12 1.326(2) . ?
F5 C23 1.339(2) . ?
F4 C23 1.344(2) . ?
O1 C16 1.230(2) . ?
F6 C23 1.344(2) . ?
F1 C12 1.340(3) . ?
N1 C6 1.365(2) . ?
N1 C7 1.382(2) . ?
N1 H1 0.8800 . ?
N2 C16 1.364(2) . ?
N2 C18 1.417(2) . ?
N2 H2 0.8800 . ?
F2 C12 1.314(3) . ?
C6 C1 1.399(3) . ?
C6 C5 1.419(2) . ?
C16 C7 1.476(3) . ?
C5 C4 1.411(3) . ?
C5 C8 1.428(3) . ?
C7 C8 1.388(2) . ?
C13 C14 1.384(3) . ?
C13 C11 1.390(3) . ?
C13 C12 1.504(2) . ?
C15 C14 1.397(2) . ?
C15 C9 1.397(3) . ?
C15 H15 0.9500 . ?
C9 C10 1.398(3) . ?
C9 C8 1.490(2) . ?
C18 C17 1.395(3) . ?
C18 C19 1.398(3) . ?
C14 H14 0.9500 . ?
C17 C22 1.388(3) . ?
C17 H17 0.9500 . ?
C11 C10 1.391(2) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C1 C2 1.374(3) . ?
C1 H1A 0.9500 . ?
C4 C3 1.381(3) . ?
C4 H4 0.9500 . ?
C2 C3 1.413(3) . ?
C2 H2A 0.9500 . ?
C22 C21 1.394(3) . ?
C22 H22 0.9500 . ?
C19 C20 1.398(3) . ?
C19 H19 0.9500 . ?
C3 H3 0.9500 . ?
C21 C20 1.378(3) . ?
C21 C23 1.491(3) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 109.45(14) . . ?
C6 N1 H1 125.3 . . ?
C7 N1 H1 125.3 . . ?
C16 N2 C18 125.25(15) . . ?
C16 N2 H2 117.4 . . ?
C18 N2 H2 117.4 . . ?
N1 C6 C1 130.20(16) . . ?
N1 C6 C5 107.49(16) . . ?
C1 C6 C5 122.31(17) . . ?
O1 C16 N2 122.23(17) . . ?
O1 C16 C7 120.64(16) . . ?
N2 C16 C7 117.13(15) . . ?
C4 C5 C6 118.93(17) . . ?
C4 C5 C8 133.56(16) . . ?
C6 C5 C8 107.51(15) . . ?
N1 C7 C8 109.34(16) . . ?
N1 C7 C16 115.84(15) . . ?
C8 C7 C16 134.71(17) . . ?
C14 C13 C11 120.51(16) . . ?
C14 C13 C12 120.32(17) . . ?
C11 C13 C12 119.17(16) . . ?
C14 C15 C9 120.41(16) . . ?
C14 C15 H15 119.8 . . ?
C9 C15 H15 119.8 . . ?
C15 C9 C10 118.78(16) . . ?
C15 C9 C8 121.62(16) . . ?
C10 C9 C8 119.51(16) . . ?
C17 C18 C19 119.91(17) . . ?
C17 C18 N2 121.48(17) . . ?
C19 C18 N2 118.57(16) . . ?
C7 C8 C5 106.20(15) . . ?
C7 C8 C9 130.19(17) . . ?
C5 C8 C9 123.61(15) . . ?
C13 C14 C15 119.86(17) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C22 C17 C18 119.37(17) . . ?
C22 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C11 C10 119.52(17) . . ?
C13 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C10 C9 120.90(17) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C2 C1 C6 117.30(17) . . ?
C2 C1 H1A 121.3 . . ?
C6 C1 H1A 121.3 . . ?
C3 C4 C5 118.61(17) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C1 C2 C3 121.70(18) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C17 C22 C21 120.34(17) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C18 C19 C20 120.44(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C4 C3 C2 121.16(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C20 C21 C22 120.87(18) . . ?
C20 C21 C23 120.71(18) . . ?
C22 C21 C23 118.42(17) . . ?
F2 C12 F3 107.72(18) . . ?
F2 C12 F1 106.73(19) . . ?
F3 C12 F1 104.34(16) . . ?
F2 C12 C13 112.50(16) . . ?
F3 C12 C13 113.12(16) . . ?
F1 C12 C13 111.88(17) . . ?
C21 C20 C19 119.06(18) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
F5 C23 F4 105.95(17) . . ?
F5 C23 F6 106.09(17) . . ?
F4 C23 F6 105.76(16) . . ?
F5 C23 C21 112.85(16) . . ?
F4 C23 C21 113.76(17) . . ?
F6 C23 C21 111.82(18) . . ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.066



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_MAB_111_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127606'
loop_
_audit_author_name
_audit_author_address
'Dr. Thangavel Vijayakanth'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2025-04-02 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            'C15 H11 F3 N2 O4'
_chemical_formula_weight         340.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3389(15)
_cell_length_b                   5.3319(10)
_cell_length_c                   30.853(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.827(6)
_cell_angle_gamma                90
_cell_volume                     1370.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2426
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      22.81

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6148
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13561
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.322
_diffrn_reflns_theta_max         24.817
_diffrn_reflns_theta_full        24.817
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2344
_reflns_number_gt                1808
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0406P)²+1.1078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2344
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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
F1 F 0.76240(17) 0.6864(3) 0.82870(5) 0.0330(4) Uani 1 1 d . . . . .
F2 F 0.52839(19) 0.5727(3) 0.84615(5) 0.0403(5) Uani 1 1 d . . . . .
F3 F 0.5962(2) 0.9600(3) 0.85100(5) 0.0460(5) Uani 1 1 d . . . . .
O4 O 0.8360(2) 0.5039(3) 0.52273(6) 0.0286(5) Uani 1 1 d . . . . .
O3 O 0.8360(2) 0.8391(3) 0.57092(6) 0.0294(5) Uani 1 1 d . . . . .
O2 O 0.3149(2) 0.0496(3) 0.53493(6) 0.0292(5) Uani 1 1 d . . . . .
O1 O 0.1909(2) 0.2430(3) 0.58472(6) 0.0290(5) Uani 1 1 d . . . . .
N2 N 0.3082(3) 0.2174(4) 0.56240(6) 0.0208(5) Uani 1 1 d . . . . .
N1 N 0.3311(2) 0.8592(4) 0.65583(6) 0.0217(5) Uani 1 1 d . . . . .
H1 H 0.2997 1.0081 0.6465 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5740(3) 0.6163(5) 0.74941(8) 0.0196(6) Uani 1 1 d . . . . .
H3 H 0.6419 0.4781 0.7567 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4464(3) 0.9999(4) 0.76971(8) 0.0188(6) Uani 1 1 d . . . . .
H4 H 0.4270 1.1252 0.7907 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3774(3) 1.0200(4) 0.72823(8) 0.0178(5) Uani 1 1 d . . . . .
H5 H 0.3109 1.1599 0.7209 0.021 Uiso 1 1 calc R U . . .
C7 C 0.4039(3) 0.8375(4) 0.69678(8) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.5442(3) 0.7958(4) 0.78070(8) 0.0180(5) Uani 1 1 d . . . . .
C6 C 0.5061(3) 0.6365(4) 0.70784(8) 0.0185(5) Uani 1 1 d . . . . .
H6 H 0.5288 0.5138 0.6867 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4437(3) 0.3884(4) 0.56825(8) 0.0185(5) Uani 1 1 d . . . . .
C13 C 0.6978(3) 0.5033(5) 0.54531(8) 0.0206(6) Uani 1 1 d . . . . .
C9 C 0.4419(3) 0.5880(4) 0.59799(7) 0.0180(5) Uani 1 1 d . . . . .
C14 C 0.6986(3) 0.7034(5) 0.57368(8) 0.0209(6) Uani 1 1 d . . . . .
C11 C 0.5725(3) 0.3409(5) 0.54164(8) 0.0208(6) Uani 1 1 d . . . . .
H11 H 0.5719 0.2028 0.5222 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5753(3) 0.7493(5) 0.60031(8) 0.0209(6) Uani 1 1 d . . . . .
H12 H 0.5799 0.8870 0.6199 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3048(3) 0.6434(5) 0.62768(8) 0.0219(6) Uani 1 1 d . . . . .
H8A H 0.2053 0.6711 0.6095 0.026 Uiso 1 1 calc R U . . .
H8B H 0.2875 0.4940 0.6459 0.026 Uiso 1 1 calc R U . . .
C1 C 0.6076(3) 0.7573(5) 0.82609(8) 0.0241(6) Uani 1 1 d . . . . .
C15 C 0.9258(3) 0.7175(6) 0.53820(9) 0.0312(7) Uani 1 1 d . . . . .
H15A H 0.9429 0.8349 0.5140 0.037 Uiso 1 1 calc R U . . .
H15B H 1.0320 0.6640 0.5507 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.344(3) . ?
F2 C1 1.352(3) . ?
F3 C1 1.332(3) . ?
O4 C13 1.376(3) . ?
O4 C15 1.432(3) . ?
O3 C14 1.361(3) . ?
O3 C15 1.441(3) . ?
O2 N2 1.236(3) . ?
O1 N2 1.231(3) . ?
N2 C10 1.456(3) . ?
N1 C7 1.379(3) . ?
N1 C8 1.452(3) . ?
N1 H1 0.8800 . ?
C3 C6 1.380(3) . ?
C3 C2 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 C2 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.399(3) . ?
C5 H5 0.9500 . ?
C7 C6 1.401(3) . ?
C2 C1 1.486(4) . ?
C6 H6 0.9500 . ?
C10 C9 1.406(3) . ?
C10 C11 1.407(3) . ?
C13 C11 1.357(4) . ?
C13 C14 1.380(4) . ?
C9 C12 1.405(3) . ?
C9 C8 1.529(3) . ?
C14 C12 1.369(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O4 C15 105.71(19) . . ?
C14 O3 C15 105.8(2) . . ?
O1 N2 O2 121.9(2) . . ?
O1 N2 C10 119.6(2) . . ?
O2 N2 C10 118.5(2) . . ?
C7 N1 C8 121.9(2) . . ?
C7 N1 H1 119.1 . . ?
C8 N1 H1 119.1 . . ?
C6 C3 C2 120.8(2) . . ?
C6 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C2 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C2 C4 H4 120.0 . . ?
C4 C5 C7 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C7 C5 H5 119.5 . . ?
N1 C7 C5 120.0(2) . . ?
N1 C7 C6 121.5(2) . . ?
C5 C7 C6 118.6(2) . . ?
C3 C2 C4 119.4(2) . . ?
C3 C2 C1 119.4(2) . . ?
C4 C2 C1 121.0(2) . . ?
C3 C6 C7 120.2(2) . . ?
C3 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C9 C10 C11 123.4(2) . . ?
C9 C10 N2 121.5(2) . . ?
C11 C10 N2 115.2(2) . . ?
C11 C13 O4 128.3(2) . . ?
C11 C13 C14 121.7(2) . . ?
O4 C13 C14 110.0(2) . . ?
C12 C9 C10 117.6(2) . . ?
C12 C9 C8 117.7(2) . . ?
C10 C9 C8 124.7(2) . . ?
O3 C14 C12 127.0(2) . . ?
O3 C14 C13 110.4(2) . . ?
C12 C14 C13 122.6(2) . . ?
C13 C11 C10 116.3(2) . . ?
C13 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
C14 C12 C9 118.4(2) . . ?
C14 C12 H12 120.8 . . ?
C9 C12 H12 120.8 . . ?
N1 C8 C9 114.6(2) . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
F3 C1 F1 106.8(2) . . ?
F3 C1 F2 106.0(2) . . ?
F1 C1 F2 104.9(2) . . ?
F3 C1 C2 113.5(2) . . ?
F1 C1 C2 113.0(2) . . ?
F2 C1 C2 111.9(2) . . ?
O4 C15 O3 108.0(2) . . ?
O4 C15 H15A 110.1 . . ?
O3 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
O3 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_TRI_a
_database_code_depnum_ccdc_archive 'CCDC 2127604'
loop_
_audit_author_name
_audit_author_address
'Dr. Thangavel Vijayakanth'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2025-04-02 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            'C39 H50 Cl F6 N3 O'
_chemical_formula_weight         726.27

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   24.4975(12)
_cell_length_b                   8.6281(5)
_cell_length_c                   18.2798(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.476(2)
_cell_angle_gamma                90
_cell_volume                     3705.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8332
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.67

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5193
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50556
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.1637
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6538
_reflns_number_gt                4365
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0262P)²+2.7889P] 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       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6538
_refine_ls_number_parameters     456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0949
_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
Cl Cl 0.16992(3) 0.17260(8) 0.38664(4) 0.02098(19) Uani 1 1 d . . . . .
F5 F -0.00370(7) 0.21946(18) 0.69638(10) 0.0305(4) Uani 1 1 d . . . . .
F3 F 0.55880(6) 0.5354(2) 0.85467(9) 0.0342(5) Uani 1 1 d . . . . .
F6 F 0.03761(7) 0.0087(2) 0.74394(10) 0.0342(5) Uani 1 1 d . . . . .
F4 F -0.01844(7) 0.0119(2) 0.62955(10) 0.0381(5) Uani 1 1 d . . . . .
O1 O 0.26917(7) 0.3738(2) 0.66733(10) 0.0183(5) Uani 1 1 d . . . . .
F2 F 0.51143(8) 0.7192(2) 0.88517(11) 0.0481(6) Uani 1 1 d . . . . .
F1 F 0.50140(8) 0.4867(3) 0.92025(10) 0.0494(6) Uani 1 1 d . . . . .
N1 N 0.27743(9) 0.3465(3) 0.47340(12) 0.0165(5) Uani 1 1 d . . . . .
H1 H 0.2450 0.3050 0.4469 0.020 Uiso 1 1 calc R U . . .
N2 N 0.20569(9) 0.2650(3) 0.56423(12) 0.0155(5) Uani 1 1 d . . . . .
H2 H 0.1998 0.2435 0.5155 0.019 Uiso 1 1 calc R U . . .
N1A N 0.20517(9) 0.7209(2) 0.77009(12) 0.0136(5) Uani 1 1 d . . . . .
C21 C 0.16728(11) 0.2244(3) 0.67436(15) 0.0148(6) Uani 1 1 d . . . . .
H21 H 0.2019 0.2574 0.7095 0.018 Uiso 1 1 calc R U . . .
C20 C 0.12188(11) 0.1808(3) 0.70054(15) 0.0167(6) Uani 1 1 d . . . . .
H20 H 0.1253 0.1846 0.7536 0.020 Uiso 1 1 calc R U . . .
C15 C 0.25571(11) 0.3381(3) 0.59962(16) 0.0145(6) Uani 1 1 d . . . . .
C14 C 0.29307(11) 0.3746(3) 0.55132(15) 0.0137(6) Uani 1 1 d . . . . .
C13A C 0.15690(11) 0.6130(3) 0.72978(15) 0.0150(6) Uani 1 1 d . . . . .
H13A H 0.1702 0.5482 0.6936 0.018 Uiso 1 1 calc R U . . .
H13B H 0.1491 0.5426 0.7684 0.018 Uiso 1 1 calc R U . . .
C6 C 0.43432(11) 0.4020(3) 0.77725(16) 0.0188(7) Uani 1 1 d . . . . .
H6 H 0.4423 0.3255 0.8162 0.023 Uiso 1 1 calc R U . . .
C19 C 0.07133(11) 0.1314(3) 0.64991(16) 0.0165(6) Uani 1 1 d . . . . .
C8 C 0.36383(11) 0.4571(3) 0.50418(15) 0.0164(6) Uani 1 1 d . . . . .
C5 C 0.39545(11) 0.3720(3) 0.70734(15) 0.0178(7) Uani 1 1 d . . . . .
H5 H 0.3769 0.2742 0.6987 0.021 Uiso 1 1 calc R U . . .
C5A C 0.18749(11) 0.8281(3) 0.82510(15) 0.0160(6) Uani 1 1 d . . . . .
H5A1 H 0.2215 0.8864 0.8543 0.019 Uiso 1 1 calc R U . . .
H5A2 H 0.1600 0.9044 0.7949 0.019 Uiso 1 1 calc R U . . .
C9A C 0.22252(11) 0.8260(3) 0.71357(15) 0.0151(6) Uani 1 1 d . . . . .
H9A1 H 0.1890 0.8883 0.6862 0.018 Uiso 1 1 calc R U . . .
H9A2 H 0.2520 0.8988 0.7426 0.018 Uiso 1 1 calc R U . . .
C17 C 0.11151(11) 0.1684(3) 0.54609(16) 0.0205(7) Uani 1 1 d . . . . .
H17 H 0.1078 0.1635 0.4930 0.025 Uiso 1 1 calc R U . . .
C10A C 0.24538(12) 0.7444(3) 0.65490(15) 0.0172(7) Uani 1 1 d . . . . .
H10A H 0.2162 0.6722 0.6246 0.021 Uiso 1 1 calc R U . . .
H10B H 0.2795 0.6831 0.6812 0.021 Uiso 1 1 calc R U . . .
C16 C 0.16251(11) 0.2202(3) 0.59678(15) 0.0136(6) Uani 1 1 d . . . . .
C1A C 0.25415(11) 0.6157(3) 0.81150(15) 0.0157(6) Uani 1 1 d . . . . .
H1A1 H 0.2422 0.5567 0.8508 0.019 Uiso 1 1 calc R U . . .
H1A2 H 0.2609 0.5398 0.7743 0.019 Uiso 1 1 calc R U . . .
C12A C 0.30718(11) 0.9751(3) 0.64283(16) 0.0208(7) Uani 1 1 d . . . . .
H12A H 0.2926 1.0421 0.6763 0.031 Uiso 1 1 calc R U . . .
H12B H 0.3186 1.0389 0.6053 0.031 Uiso 1 1 calc R U . . .
H12C H 0.3402 0.9171 0.6734 0.031 Uiso 1 1 calc R U . . .
C4 C 0.38301(11) 0.4821(3) 0.64953(15) 0.0159(6) Uani 1 1 d . . . . .
C14A C 0.10136(11) 0.6887(3) 0.68637(15) 0.0165(6) Uani 1 1 d . . . . .
H14A H 0.1075 0.7559 0.6456 0.020 Uiso 1 1 calc R U . . .
H14B H 0.0868 0.7537 0.7213 0.020 Uiso 1 1 calc R U . . .
C1 C 0.46133(11) 0.5439(3) 0.78980(15) 0.0178(7) Uani 1 1 d . . . . .
C13 C 0.32037(11) 0.3935(3) 0.44420(16) 0.0180(7) Uani 1 1 d . . . . .
C18 C 0.06687(12) 0.1246(3) 0.57292(16) 0.0211(7) Uani 1 1 d . . . . .
H18 H 0.0325 0.0893 0.5381 0.025 Uiso 1 1 calc R U . . .
C7 C 0.34628(11) 0.4433(3) 0.57259(15) 0.0160(6) Uani 1 1 d . . . . .
C15A C 0.05831(11) 0.5625(3) 0.65164(16) 0.0185(7) Uani 1 1 d . . . . .
H15A H 0.0748 0.4926 0.6206 0.022 Uiso 1 1 calc R U . . .
H15B H 0.0507 0.5003 0.6932 0.022 Uiso 1 1 calc R U . . .
C11A C 0.26101(12) 0.8625(3) 0.60175(16) 0.0193(7) Uani 1 1 d . . . . .
H11A H 0.2740 0.8063 0.5626 0.023 Uiso 1 1 calc R U . . .
H11B H 0.2265 0.9219 0.5752 0.023 Uiso 1 1 calc R U . . .
C3 C 0.40972(11) 0.6254(3) 0.66415(16) 0.0204(7) Uani 1 1 d . . . . .
H3 H 0.4013 0.7029 0.6256 0.024 Uiso 1 1 calc R U . . .
C2A C 0.31021(11) 0.6959(3) 0.84988(16) 0.0209(7) Uani 1 1 d . . . . .
H2A1 H 0.3043 0.7750 0.8861 0.025 Uiso 1 1 calc R U . . .
H2A2 H 0.3246 0.7489 0.8110 0.025 Uiso 1 1 calc R U . . .
C12 C 0.32489(12) 0.3797(3) 0.37004(16) 0.0199(7) Uani 1 1 d . . . . .
H12 H 0.2953 0.3347 0.3304 0.024 Uiso 1 1 calc R U . . .
C9 C 0.41354(12) 0.5118(3) 0.48873(17) 0.0221(7) Uani 1 1 d . . . . .
H9 H 0.4436 0.5556 0.5281 0.027 Uiso 1 1 calc R U . . .
C2 C 0.44854(11) 0.6574(3) 0.73422(16) 0.0225(7) Uani 1 1 d . . . . .
H2A H 0.4661 0.7563 0.7438 0.027 Uiso 1 1 calc R U . . .
C11 C 0.37388(12) 0.4341(3) 0.35690(17) 0.0237(7) Uani 1 1 d . . . . .
H11 H 0.3783 0.4266 0.3070 0.028 Uiso 1 1 calc R U . . .
C22 C 0.02219(12) 0.0926(3) 0.67929(17) 0.0222(7) Uani 1 1 d . . . . .
C10 C 0.41770(12) 0.5004(3) 0.41534(17) 0.0238(7) Uani 1 1 d . . . . .
H10 H 0.4508 0.5382 0.4041 0.029 Uiso 1 1 calc R U . . .
C3A C 0.35372(12) 0.5769(3) 0.89238(16) 0.0240(7) Uani 1 1 d . . . . .
H3A1 H 0.3523 0.4858 0.8589 0.029 Uiso 1 1 calc R U . . .
H3A2 H 0.3923 0.6226 0.9033 0.029 Uiso 1 1 calc R U . . .
C23 C 0.50708(12) 0.5719(4) 0.86217(18) 0.0260(7) Uani 1 1 d . . . . .
C6A C 0.16094(12) 0.7521(3) 0.88137(16) 0.0190(7) Uani 1 1 d . . . . .
H6A1 H 0.1864 0.6697 0.9097 0.023 Uiso 1 1 calc R U . . .
H6A2 H 0.1242 0.7040 0.8537 0.023 Uiso 1 1 calc R U . . .
C4A C 0.34422(12) 0.5232(4) 0.96642(16) 0.0276(8) Uani 1 1 d . . . . .
H4A1 H 0.3496 0.6105 1.0020 0.041 Uiso 1 1 calc R U . . .
H4A2 H 0.3715 0.4411 0.9887 0.041 Uiso 1 1 calc R U . . .
H4A3 H 0.3054 0.4830 0.9566 0.041 Uiso 1 1 calc R U . . .
C8A C 0.11625(12) 0.8097(4) 0.98664(16) 0.0264(7) Uani 1 1 d . . . . .
H8A1 H 0.0782 0.7820 0.9546 0.040 Uiso 1 1 calc R U . . .
H8A2 H 0.1131 0.8891 1.0236 0.040 Uiso 1 1 calc R U . . .
H8A3 H 0.1349 0.7176 1.0139 0.040 Uiso 1 1 calc R U . . .
C16A C 0.00254(12) 0.6276(4) 0.60189(17) 0.0276(8) Uani 1 1 d . . . . .
H16A H -0.0147 0.6940 0.6327 0.041 Uiso 1 1 calc R U . . .
H16B H -0.0234 0.5421 0.5804 0.041 Uiso 1 1 calc R U . . .
H16C H 0.0098 0.6886 0.5604 0.041 Uiso 1 1 calc R U . . .
C7A C 0.15133(12) 0.8727(3) 0.93670(16) 0.0213(7) Uani 1 1 d . . . . .
H7A1 H 0.1315 0.9631 0.9077 0.026 Uiso 1 1 calc R U . . .
H7A2 H 0.1886 0.9086 0.9696 0.026 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
F5 C22 1.346(3) . ?
F3 C23 1.350(3) . ?
F6 C22 1.345(3) . ?
F4 C22 1.337(3) . ?
O1 C15 1.226(3) . ?
F2 C23 1.333(3) . ?
F1 C23 1.331(3) . ?
N1 C13 1.369(3) . ?
N1 C14 1.387(3) . ?
N1 H1 0.8800 . ?
N2 C15 1.367(3) . ?
N2 C16 1.407(3) . ?
N2 H2 0.8800 . ?
N1A C5A 1.517(3) . ?
N1A C13A 1.521(3) . ?
N1A C9A 1.523(3) . ?
N1A C1A 1.524(3) . ?
C21 C20 1.382(4) . ?
C21 C16 1.390(4) . ?
C21 H21 0.9500 . ?
C20 C19 1.386(4) . ?
C20 H20 0.9500 . ?
C15 C14 1.475(4) . ?
C14 C7 1.384(4) . ?
C13A C14A 1.515(3) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C6 C1 1.380(4) . ?
C6 C5 1.384(4) . ?
C6 H6 0.9500 . ?
C19 C18 1.382(4) . ?
C19 C22 1.489(4) . ?
C8 C13 1.405(4) . ?
C8 C9 1.407(4) . ?
C8 C7 1.438(4) . ?
C5 C4 1.389(4) . ?
C5 H5 0.9500 . ?
C5A C6A 1.514(4) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C9A C10A 1.516(4) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C17 C18 1.372(4) . ?
C17 C16 1.401(4) . ?
C17 H17 0.9500 . ?
C10A C11A 1.530(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C1A C2A 1.520(4) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C12A C11A 1.519(4) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C4 C3 1.389(4) . ?
C4 C7 1.477(4) . ?
C14A C15A 1.523(4) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C1 C2 1.381(4) . ?
C1 C23 1.491(4) . ?
C13 C12 1.396(4) . ?
C18 H18 0.9500 . ?
C15A C16A 1.518(4) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C3 C2 1.389(4) . ?
C3 H3 0.9500 . ?
C2A C3A 1.525(4) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C12 C11 1.372(4) . ?
C12 H12 0.9500 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C2 H2A 0.9500 . ?
C11 C10 1.404(4) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C3A C4A 1.510(4) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C6A C7A 1.515(4) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
C8A C7A 1.520(4) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C14 109.2(2) . . ?
C13 N1 H1 125.4 . . ?
C14 N1 H1 125.4 . . ?
C15 N2 C16 127.4(2) . . ?
C15 N2 H2 116.3 . . ?
C16 N2 H2 116.3 . . ?
C5A N1A C13A 111.44(19) . . ?
C5A N1A C9A 105.87(19) . . ?
C13A N1A C9A 111.3(2) . . ?
C5A N1A C1A 111.5(2) . . ?
C13A N1A C1A 105.71(19) . . ?
C9A N1A C1A 111.08(19) . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
O1 C15 N2 122.8(2) . . ?
O1 C15 C14 121.0(2) . . ?
N2 C15 C14 116.1(2) . . ?
C7 C14 N1 109.1(2) . . ?
C7 C14 C15 128.2(2) . . ?
N1 C14 C15 122.7(2) . . ?
C14A C13A N1A 116.7(2) . . ?
C14A C13A H13A 108.1 . . ?
N1A C13A H13A 108.1 . . ?
C14A C13A H13B 108.1 . . ?
N1A C13A H13B 108.1 . . ?
H13A C13A H13B 107.3 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 C22 121.3(3) . . ?
C20 C19 C22 119.3(3) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 C7 107.4(2) . . ?
C9 C8 C7 133.8(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C6A C5A N1A 116.4(2) . . ?
C6A C5A H5A1 108.2 . . ?
N1A C5A H5A1 108.2 . . ?
C6A C5A H5A2 108.2 . . ?
N1A C5A H5A2 108.2 . . ?
H5A1 C5A H5A2 107.3 . . ?
C10A C9A N1A 115.7(2) . . ?
C10A C9A H9A1 108.4 . . ?
N1A C9A H9A1 108.4 . . ?
C10A C9A H9A2 108.4 . . ?
N1A C9A H9A2 108.4 . . ?
H9A1 C9A H9A2 107.4 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C9A C10A C11A 110.4(2) . . ?
C9A C10A H10A 109.6 . . ?
C11A C10A H10A 109.6 . . ?
C9A C10A H10B 109.6 . . ?
C11A C10A H10B 109.6 . . ?
H10A C10A H10B 108.1 . . ?
C21 C16 C17 119.0(2) . . ?
C21 C16 N2 124.6(2) . . ?
C17 C16 N2 116.4(2) . . ?
C2A C1A N1A 116.0(2) . . ?
C2A C1A H1A1 108.3 . . ?
N1A C1A H1A1 108.3 . . ?
C2A C1A H1A2 108.3 . . ?
N1A C1A H1A2 108.3 . . ?
H1A1 C1A H1A2 107.4 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C7 120.8(2) . . ?
C5 C4 C7 120.8(2) . . ?
C13A C14A C15A 108.8(2) . . ?
C13A C14A H14A 109.9 . . ?
C15A C14A H14A 109.9 . . ?
C13A C14A H14B 109.9 . . ?
C15A C14A H14B 109.9 . . ?
H14A C14A H14B 108.3 . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 C23 119.7(3) . . ?
C2 C1 C23 119.6(3) . . ?
N1 C13 C12 129.4(3) . . ?
N1 C13 C8 107.9(2) . . ?
C12 C13 C8 122.7(3) . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C7 C8 106.4(2) . . ?
C14 C7 C4 129.5(3) . . ?
C8 C7 C4 123.9(2) . . ?
C16A C15A C14A 112.6(2) . . ?
C16A C15A H15A 109.1 . . ?
C14A C15A H15A 109.1 . . ?
C16A C15A H15B 109.1 . . ?
C14A C15A H15B 109.1 . . ?
H15A C15A H15B 107.8 . . ?
C12A C11A C10A 113.4(2) . . ?
C12A C11A H11A 108.9 . . ?
C10A C11A H11A 108.9 . . ?
C12A C11A H11B 108.9 . . ?
C10A C11A H11B 108.9 . . ?
H11A C11A H11B 107.7 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C1A C2A C3A 109.7(2) . . ?
C1A C2A H2A1 109.7 . . ?
C3A C2A H2A1 109.7 . . ?
C1A C2A H2A2 109.7 . . ?
C3A C2A H2A2 109.7 . . ?
H2A1 C2A H2A2 108.2 . . ?
C11 C12 C13 117.1(3) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
F4 C22 F6 106.6(2) . . ?
F4 C22 F5 105.8(2) . . ?
F6 C22 F5 105.5(2) . . ?
F4 C22 C19 113.2(2) . . ?
F6 C22 C19 112.5(2) . . ?
F5 C22 C19 112.6(2) . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C4A C3A C2A 113.6(2) . . ?
C4A C3A H3A1 108.8 . . ?
C2A C3A H3A1 108.8 . . ?
C4A C3A H3A2 108.8 . . ?
C2A C3A H3A2 108.8 . . ?
H3A1 C3A H3A2 107.7 . . ?
F1 C23 F2 107.0(3) . . ?
F1 C23 F3 105.4(2) . . ?
F2 C23 F3 105.1(2) . . ?
F1 C23 C1 113.3(2) . . ?
F2 C23 C1 114.0(3) . . ?
F3 C23 C1 111.3(2) . . ?
C5A C6A C7A 109.5(2) . . ?
C5A C6A H6A1 109.8 . . ?
C7A C6A H6A1 109.8 . . ?
C5A C6A H6A2 109.8 . . ?
C7A C6A H6A2 109.8 . . ?
H6A1 C6A H6A2 108.2 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C6A C7A C8A 112.1(2) . . ?
C6A C7A H7A1 109.2 . . ?
C8A C7A H7A1 109.2 . . ?
C6A C7A H7A2 109.2 . . ?
C8A C7A H7A2 109.2 . . ?
H7A1 C7A H7A2 107.9 . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_TRI_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2155430'
loop_
_audit_author_name
_audit_author_address
'Dr. Thangavel Vijayakanth'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2025-04-02 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            'C30 H19 F6 N3 O3'
_chemical_formula_weight         583.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.6161(11)
_cell_length_b                   18.8098(10)
_cell_length_c                   8.1114(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.641(2)
_cell_angle_gamma                90
_cell_volume                     2983.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.41

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48351
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.113
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5253
_reflns_number_gt                3550
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5253
_refine_ls_number_parameters     343
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.2210
_refine_ls_R_factor_gt           0.1755
_refine_ls_wR_factor_ref         0.5122
_refine_ls_wR_factor_gt          0.4844
_refine_ls_goodness_of_fit_ref   2.088
_refine_ls_restrained_S_all      2.171
_refine_ls_shift/su_max          0.001
_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
C22 C 0.1356(3) 0.5895(5) 0.9321(7) 0.072(3) Uani 1 1 d G U . . .
C23 C 0.1204(4) 0.6504(4) 1.0191(10) 0.099(4) Uani 1 1 d G U . . .
C24 C 0.0754(5) 0.6467(5) 1.1427(10) 0.107(4) Uani 1 1 d G U . . .
H24 H 0.0650 0.6883 1.2022 0.129 Uiso 1 1 calc R U . . .
C25 C 0.0457(5) 0.5821(5) 1.1794(9) 0.144(6) Uani 1 1 d G U . . .
H25 H 0.0150 0.5796 1.2640 0.172 Uiso 1 1 calc R U . . .
C26 C 0.0610(5) 0.5212(4) 1.0925(10) 0.175(10) Uani 1 1 d G . . . .
H26 H 0.0406 0.4771 1.1176 0.210 Uiso 1 1 calc R U . . .
C27 C 0.1059(4) 0.5249(4) 0.9688(8) 0.123(6) Uani 1 1 d G . . . .
H27 H 0.1163 0.4833 0.9094 0.148 Uiso 1 1 calc R U . . .
N1 N 0.1811(3) 0.5275(3) 0.6842(7) 0.0347(15) Uani 1 1 d . . . . .
C2 C 0.32916(18) 0.37135(19) 0.8203(6) 0.0427(19) Uani 1 1 d G . . . .
C3 C 0.2605(2) 0.35269(16) 0.7987(6) 0.0392(18) Uani 1 1 d G . . . .
H3 H 0.2469 0.3049 0.8153 0.047 Uiso 1 1 calc R U . . .
C4 C 0.21151(15) 0.4040(2) 0.7529(5) 0.0301(15) Uani 1 1 d G . . . .
H4 H 0.1646 0.3912 0.7382 0.036 Uiso 1 1 calc R U . . .
C5 C 0.23128(17) 0.47391(17) 0.7287(5) 0.0281(15) Uani 1 1 d G . . . .
C6 C 0.29999(19) 0.49257(16) 0.7502(6) 0.0337(16) Uani 1 1 d G . . . .
H6 H 0.3135 0.5404 0.7337 0.040 Uiso 1 1 calc R U . . .
C7 C 0.34892(14) 0.4413(2) 0.7960(6) 0.0429(18) Uani 1 1 d G . . . .
H7 H 0.3959 0.4541 0.8108 0.051 Uiso 1 1 calc R U . . .
O1 O 0.0757(2) 0.5565(2) 0.5736(5) 0.0336(12) Uani 1 1 d . . . . .
C16 C 0.24520(18) 0.4565(2) 0.3482(6) 0.0339(16) Uani 1 1 d G . . . .
C17 C 0.2562(3) 0.5281(2) 0.3176(7) 0.053(2) Uani 1 1 d G . . . .
H17 H 0.2192 0.5608 0.3159 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3214(3) 0.5519(3) 0.2895(9) 0.104(5) Uani 1 1 d G . . . .
H18 H 0.3289 0.6009 0.2686 0.125 Uiso 1 1 calc R U . . .
C19 C 0.3755(3) 0.5041(4) 0.2919(9) 0.100(5) Uani 1 1 d G . . . .
C20 C 0.3644(2) 0.4325(4) 0.3225(9) 0.080(3) Uani 1 1 d G . . . .
H20 H 0.4014 0.3998 0.3241 0.096 Uiso 1 1 calc R U . . .
C21 C 0.2993(2) 0.4087(2) 0.3506(7) 0.050(2) Uani 1 1 d G . . . .
H21 H 0.2918 0.3597 0.3715 0.060 Uiso 1 1 calc R U . . .
N2 N 0.0653(2) 0.4202(3) 0.4220(6) 0.0251(12) Uani 1 1 d . . . . .
H2 H 0.0267 0.4289 0.4662 0.030 Uiso 1 1 calc R U . . .
F1 F 0.4295(3) 0.3379(3) 0.9788(9) 0.100(2) Uani 1 1 d . . . . .
C14 C 0.0285(3) 0.3195(4) 0.2378(8) 0.0326(16) Uani 1 1 d . . . . .
H14 H -0.0177 0.3184 0.2644 0.039 Uiso 1 1 calc R U . . .
F2 F 0.4285(4) 0.3116(5) 0.7397(11) 0.142(3) Uani 1 1 d . . . . .
F3 F 0.3634(4) 0.2589(4) 0.881(2) 0.245(9) Uani 1 1 d . . . . .
C30 C 0.1751(3) 0.4302(3) 0.3638(7) 0.0275(15) Uani 1 1 d . . . . .
C8 C 0.1260(3) 0.5175(3) 0.5754(7) 0.0272(15) Uani 1 1 d . . . . .
C9 C 0.1262(3) 0.4565(3) 0.4554(8) 0.0255(14) Uani 1 1 d . . . . .
C1 C 0.3803(5) 0.3185(5) 0.8692(14) 0.072(3) Uani 1 1 d . . . . .
C28 C 0.1846(4) 0.5948(5) 0.7729(12) 0.068(3) Uani 1 1 d . . . . .
H28A H 0.1682 0.6339 0.6979 0.082 Uiso 1 1 calc R U . . .
H28B H 0.2325 0.6051 0.8139 0.082 Uiso 1 1 calc R U . . .
O2 O 0.1970(6) 0.7304(5) 0.8977(16) 0.149(4) Uani 1 1 d . U . . .
N3 N 0.1460(6) 0.7081(8) 0.9867(17) 0.128(5) Uani 1 1 d . . . . .
O3 O 0.1229(6) 0.7787(6) 1.0052(15) 0.180(5) Uani 1 1 d . U . . .
C10 C 0.1435(3) 0.3723(3) 0.2706(7) 0.0224(14) Uani 1 1 d . . . . .
C15 C 0.0754(3) 0.3686(3) 0.3090(7) 0.0233(14) Uani 1 1 d . . . . .
C13 C 0.0537(3) 0.2727(4) 0.1260(8) 0.0342(16) Uani 1 1 d . . . . .
H13 H 0.0238 0.2380 0.0746 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1221(3) 0.2749(4) 0.0862(8) 0.0369(17) Uani 1 1 d . . . . .
H12 H 0.1372 0.2414 0.0094 0.044 Uiso 1 1 calc R U . . .
C11 C 0.1667(3) 0.3231(4) 0.1540(8) 0.0333(16) Uani 1 1 d . . . . .
H11 H 0.2126 0.3242 0.1248 0.040 Uiso 1 1 calc R U . . .
F4 F 0.4696(5) 0.5773(7) 0.3503(16) 0.234(8) Uani 1 1 d . . . . .
F5 F 0.4917(7) 0.4764(9) 0.271(3) 0.287(12) Uani 1 1 d . . . . .
F6 F 0.4493(9) 0.5516(13) 0.1171(18) 0.279(12) Uani 1 1 d . . . . .
C29 C 0.4404(11) 0.5352(16) 0.250(3) 0.194(12) 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
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C22 C28 1.674(12) . ?
C23 N3 1.233(16) . ?
C23 C24 1.3900 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 C27 1.3900 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
N1 C8 1.351(8) . ?
N1 C5 1.436(6) . ?
N1 C28 1.455(9) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C2 C1 1.445(9) . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
O1 C8 1.229(7) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C16 C30 1.476(7) . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 C29 1.466(15) . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
N2 C15 1.360(7) . ?
N2 C9 1.384(8) . ?
N2 H2 0.8800 . ?
F1 C1 1.310(11) . ?
C14 C13 1.384(9) . ?
C14 C15 1.394(9) . ?
C14 H14 0.9500 . ?
F2 C1 1.475(13) . ?
F3 C1 1.174(11) . ?
C30 C9 1.355(9) . ?
C30 C10 1.437(8) . ?
C8 C9 1.504(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O2 N3 1.348(16) . ?
N3 O3 1.414(16) . ?
C10 C15 1.399(8) . ?
C10 C11 1.424(9) . ?
C13 C12 1.406(9) . ?
C13 H13 0.9500 . ?
C12 C11 1.346(9) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
F4 C29 1.241(18) . ?
F5 C29 1.49(4) . ?
F6 C29 1.15(3) . ?

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
C23 C22 C27 120.0 . . ?
C23 C22 C28 120.2(6) . . ?
C27 C22 C28 119.7(5) . . ?
N3 C23 C24 119.4(9) . . ?
N3 C23 C22 120.6(9) . . ?
C24 C23 C22 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
C8 N1 C5 124.2(5) . . ?
C8 N1 C28 116.7(5) . . ?
C5 N1 C28 118.9(5) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 120.3(5) . . ?
C7 C2 C1 119.7(5) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 N1 120.5(3) . . ?
C6 C5 N1 119.5(3) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 C30 120.0(4) . . ?
C21 C16 C30 119.8(4) . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 C29 114.6(14) . . ?
C20 C19 C29 125.3(14) . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C15 N2 C9 108.4(5) . . ?
C15 N2 H2 125.8 . . ?
C9 N2 H2 125.8 . . ?
C13 C14 C15 115.8(6) . . ?
C13 C14 H14 122.1 . . ?
C15 C14 H14 122.1 . . ?
C9 C30 C10 105.7(5) . . ?
C9 C30 C16 129.1(5) . . ?
C10 C30 C16 125.1(5) . . ?
O1 C8 N1 121.5(6) . . ?
O1 C8 C9 119.4(5) . . ?
N1 C8 C9 119.1(5) . . ?
C30 C9 N2 110.5(5) . . ?
C30 C9 C8 132.3(5) . . ?
N2 C9 C8 117.2(5) . . ?
F3 C1 F1 114.1(9) . . ?
F3 C1 C2 119.1(9) . . ?
F1 C1 C2 116.8(8) . . ?
F3 C1 F2 100.0(11) . . ?
F1 C1 F2 91.6(8) . . ?
C2 C1 F2 109.6(8) . . ?
N1 C28 C22 108.8(7) . . ?
N1 C28 H28A 109.9 . . ?
C22 C28 H28A 109.9 . . ?
N1 C28 H28B 109.9 . . ?
C22 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C23 N3 O2 136.1(12) . . ?
C23 N3 O3 131.7(13) . . ?
O2 N3 O3 91.3(13) . . ?
C15 C10 C11 118.5(5) . . ?
C15 C10 C30 107.5(5) . . ?
C11 C10 C30 134.0(6) . . ?
N2 C15 C14 128.7(6) . . ?
N2 C15 C10 107.9(5) . . ?
C14 C15 C10 123.4(5) . . ?
C14 C13 C12 121.9(6) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C11 C12 C13 121.8(6) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C11 C10 118.5(6) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
F6 C29 F4 110(2) . . ?
F6 C29 C19 122(2) . . ?
F4 C29 C19 117.8(12) . . ?
F6 C29 F5 98.9(17) . . ?
F4 C29 F5 97(2) . . ?
C19 C29 F5 106(2) . . ?

_refine_diff_density_max         1.717
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.151

_vrf_PLAT084_TRI_a               
;
PROBLEM: ALERT A: High wR2 Value (i.e. > 0.25) ...................       0.51 Report
RESPONSE:The weakly diffractive quality of crystals leads to poor 
crystallographic refinement and hence the observed values were 
found to be high. Even though we strained our level best to solve 
this problem with more refinements, unfortunately, the problem 
remains persistent because of the poor quality of crystals.
;
_vrf_PLAT601_TRI_a               
;
PROBLEM: ALERT A: Unit Cell Contains Solvent Accessible VOIDS of .        231 Ang**
RESPONSE:As we mentioned above, the poor quality of crystals exhibits 
too many badly disordered solvent molecules, by using the 
crystallographic refinement was unable to fix them. Again, 
we tried to constrain the appropriate solvent model but we 
couldn't succeed due to the dynamic motion and disorder nature 
of the present solvent molecules in the crystal lattice.
;


####################################################################### 
# 
# 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_MAB_120422_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127605'
loop_
_audit_author_name
_audit_author_address
'Dr. Thangavel Vijayakanth'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2025-04-02 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 H24 F6 N4 O3'
_chemical_formula_weight         626.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.851(2)
_cell_length_b                   11.560(2)
_cell_length_c                   11.920(2)
_cell_angle_alpha                81.019(8)
_cell_angle_beta                 72.671(9)
_cell_angle_gamma                78.352(9)
_cell_volume                     1390.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9414
_cell_measurement_theta_min      3.91
_cell_measurement_theta_max      65.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15243
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_max         65.766
_diffrn_reflns_theta_full        65.766
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4677
_reflns_number_gt                3967
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0509P)²+2.8694P] 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       0.0067(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4677
_refine_ls_number_parameters     409
_refine_ls_number_restraints     369
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.093
_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
F6 F 0.32753(17) -0.07251(16) 0.08732(15) 0.0308(4) Uani 1 1 d . U . . .
F4 F 0.35598(19) -0.16235(15) 0.25115(16) 0.0334(5) Uani 1 1 d . U . . .
F5 F 0.51906(17) -0.10547(16) 0.11357(17) 0.0358(5) Uani 1 1 d . U . . .
O1 O 0.15776(18) 0.52682(17) 0.45034(18) 0.0222(5) Uani 1 1 d . U . . .
F1 F 0.8855(2) 0.2647(4) 0.4438(4) 0.1355(19) Uani 1 1 d . U . . .
F2 F 0.89638(18) 0.09196(18) 0.4008(2) 0.0497(6) Uani 1 1 d . U . . .
N1 N 0.0614(2) 0.3068(2) 0.5911(2) 0.0174(5) Uani 1 1 d . U . . .
H1 H -0.0110 0.3473 0.5763 0.021 Uiso 1 1 calc R U . . .
N2 N 0.2646(2) 0.3898(2) 0.3221(2) 0.0176(5) Uani 1 1 d . U . . .
O2 O 0.3790(2) 0.6380(2) 0.0427(2) 0.0409(6) Uani 1 1 d . U . . .
N4 N 0.2804(2) 0.6638(2) 0.0100(2) 0.0230(6) Uani 1 1 d . U . . .
N3 N -0.1738(2) 0.6463(2) 0.0580(2) 0.0238(6) Uani 1 1 d . U . . .
O3 O 0.2749(2) 0.7339(3) -0.0767(2) 0.0573(9) Uani 1 1 d . U . . .
F3 F 0.8727(2) 0.2384(3) 0.2792(3) 0.0892(11) Uani 1 1 d . U . . .
C7 C 0.2754(3) 0.2483(2) 0.5793(2) 0.0163(6) Uani 1 1 d . U . . .
C25 C 0.1679(3) 0.5275(2) 0.1762(2) 0.0175(6) Uani 1 1 d . U . . .
C16 C 0.2015(2) 0.4223(2) 0.4323(2) 0.0165(6) Uani 1 1 d . U . . .
C17 C 0.2992(3) 0.2692(2) 0.2933(2) 0.0169(6) Uani 1 1 d . U . . .
C6 C 0.2004(3) 0.1746(2) 0.6739(2) 0.0171(6) Uani 1 1 d . U . . .
C9 C 0.4187(3) 0.2395(2) 0.5356(2) 0.0178(6) Uani 1 1 d . U . . .
C8 C 0.1852(3) 0.3267(2) 0.5325(2) 0.0170(6) Uani 1 1 d . U . . .
C20 C 0.3629(3) 0.0442(2) 0.2166(2) 0.0192(6) Uani 1 1 d . U . . .
C26 C 0.0499(3) 0.4868(2) 0.2320(2) 0.0193(6) Uani 1 1 d . U . . .
H26 H 0.0463 0.4294 0.2988 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4979(3) 0.1293(2) 0.5427(2) 0.0202(6) Uani 1 1 d . U . . .
H10 H 0.4588 0.0616 0.5802 0.024 Uiso 1 1 calc R U . . .
C30 C 0.1644(3) 0.6111(2) 0.0774(2) 0.0182(6) Uani 1 1 d . U . . .
C18 C 0.4242(3) 0.2303(2) 0.2250(2) 0.0193(6) Uani 1 1 d . U . . .
H18 H 0.4886 0.2804 0.2050 0.023 Uiso 1 1 calc R U . . .
C27 C -0.0617(3) 0.5255(2) 0.1954(2) 0.0202(6) Uani 1 1 d . U . . .
H27 H -0.1395 0.4951 0.2380 0.024 Uiso 1 1 calc R U . . .
C5 C 0.0679(3) 0.2133(2) 0.6771(2) 0.0177(6) Uani 1 1 d . U . . .
C19 C 0.4560(3) 0.1189(3) 0.1856(2) 0.0208(6) Uani 1 1 d . U . . .
H19 H 0.5415 0.0933 0.1374 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6316(3) 0.1163(3) 0.4964(3) 0.0234(6) Uani 1 1 d . U . . .
H11 H 0.6838 0.0400 0.5014 0.028 Uiso 1 1 calc R U . . .
C28 C -0.0631(3) 0.6088(2) 0.0965(2) 0.0197(6) Uani 1 1 d . U . . .
C29 C 0.0539(3) 0.6512(2) 0.0379(2) 0.0202(6) Uani 1 1 d . U . . .
H29 H 0.0576 0.7078 -0.0295 0.024 Uiso 1 1 calc R U . . .
C4 C -0.0329(3) 0.1593(3) 0.7561(2) 0.0213(6) Uani 1 1 d . U . . .
H4 H -0.1216 0.1861 0.7560 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2065(3) 0.1932(2) 0.3264(2) 0.0187(6) Uani 1 1 d . U . . .
H22 H 0.1213 0.2186 0.3752 0.022 Uiso 1 1 calc R U . . .
C21 C 0.2384(3) 0.0810(2) 0.2884(2) 0.0195(6) Uani 1 1 d . U . . .
H21 H 0.1754 0.0293 0.3114 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6134(3) 0.3261(3) 0.4369(3) 0.0255(7) Uani 1 1 d . U . . .
H13 H 0.6533 0.3937 0.4013 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4791(3) 0.3385(3) 0.4828(3) 0.0222(6) Uani 1 1 d . U . . .
H14 H 0.4271 0.4149 0.4786 0.027 Uiso 1 1 calc R U . . .
C1 C 0.2307(3) 0.0807(3) 0.7567(2) 0.0226(6) Uani 1 1 d . U . . .
H1A H 0.3187 0.0545 0.7592 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6902(3) 0.2144(3) 0.4427(3) 0.0224(6) Uani 1 1 d . U . . .
C3 C 0.0007(3) 0.0659(3) 0.8342(3) 0.0247(6) Uani 1 1 d . U . . .
H3 H -0.0657 0.0273 0.8890 0.030 Uiso 1 1 calc R U . . .
C24 C 0.2861(3) 0.4851(2) 0.2240(3) 0.0206(6) Uani 1 1 d . U . . .
H24A H 0.3621 0.4558 0.1593 0.025 Uiso 1 1 calc R U . . .
H24B H 0.3074 0.5530 0.2518 0.025 Uiso 1 1 calc R U . . .
C23 C 0.3919(3) -0.0732(3) 0.1683(3) 0.0246(6) Uani 1 1 d . U . . .
C2 C 0.1317(3) 0.0274(3) 0.8338(3) 0.0259(7) Uani 1 1 d . U . . .
H2 H 0.1525 -0.0374 0.8884 0.031 Uiso 1 1 calc R U . . .
C32 C -0.1769(3) 0.7477(3) -0.0307(3) 0.0264(7) Uani 1 1 d . U . . .
H32A H -0.1666 0.8179 0.0002 0.040 Uiso 1 1 calc R U . . .
H32B H -0.2609 0.7624 -0.0498 0.040 Uiso 1 1 calc R U . . .
H32C H -0.1055 0.7312 -0.1021 0.040 Uiso 1 1 calc R U . . .
C15 C 0.8346(3) 0.2017(3) 0.3954(3) 0.0311(7) Uani 1 1 d . U . . .
C31 C -0.2971(3) 0.6140(3) 0.1307(3) 0.0284(7) Uani 1 1 d . U . . .
H31A H -0.2880 0.5273 0.1466 0.043 Uiso 1 1 calc R U . . .
H31B H -0.3647 0.6433 0.0893 0.043 Uiso 1 1 calc R U . . .
H31C H -0.3222 0.6493 0.2055 0.043 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
F6 C23 1.348(3) . ?
F4 C23 1.343(3) . ?
F5 C23 1.342(3) . ?
O1 C16 1.232(3) . ?
F1 C15 1.285(4) . ?
F2 C15 1.311(4) . ?
N1 C8 1.365(3) . ?
N1 C5 1.375(3) . ?
N1 H1 0.8800 . ?
N2 C16 1.360(4) . ?
N2 C17 1.437(4) . ?
N2 C24 1.475(3) . ?
O2 N4 1.212(3) . ?
N4 O3 1.218(3) . ?
N4 C30 1.468(4) . ?
N3 C28 1.377(4) . ?
N3 C31 1.447(4) . ?
N3 C32 1.453(4) . ?
F3 C15 1.347(4) . ?
C7 C8 1.378(4) . ?
C7 C6 1.447(4) . ?
C7 C9 1.472(4) . ?
C25 C26 1.393(4) . ?
C25 C30 1.407(4) . ?
C25 C24 1.518(4) . ?
C16 C8 1.491(4) . ?
C17 C18 1.384(4) . ?
C17 C22 1.397(4) . ?
C6 C1 1.404(4) . ?
C6 C5 1.409(4) . ?
C9 C10 1.392(4) . ?
C9 C14 1.403(4) . ?
C20 C19 1.390(4) . ?
C20 C21 1.390(4) . ?
C20 C23 1.495(4) . ?
C26 C27 1.375(4) . ?
C26 H26 0.9500 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C30 C29 1.385(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C27 C28 1.403(4) . ?
C27 H27 0.9500 . ?
C5 C4 1.397(4) . ?
C19 H19 0.9500 . ?
C11 C12 1.387(4) . ?
C11 H11 0.9500 . ?
C28 C29 1.399(4) . ?
C29 H29 0.9500 . ?
C4 C3 1.377(4) . ?
C4 H4 0.9500 . ?
C22 C21 1.383(4) . ?
C22 H22 0.9500 . ?
C21 H21 0.9500 . ?
C13 C14 1.381(4) . ?
C13 C12 1.392(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C1 C2 1.372(4) . ?
C1 H1A 0.9500 . ?
C12 C15 1.484(4) . ?
C3 C2 1.400(4) . ?
C3 H3 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C2 H2 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C5 108.9(2) . . ?
C8 N1 H1 125.5 . . ?
C5 N1 H1 125.5 . . ?
C16 N2 C17 124.3(2) . . ?
C16 N2 C24 117.6(2) . . ?
C17 N2 C24 117.8(2) . . ?
O2 N4 O3 121.4(2) . . ?
O2 N4 C30 119.3(2) . . ?
O3 N4 C30 119.3(2) . . ?
C28 N3 C31 119.4(2) . . ?
C28 N3 C32 119.1(2) . . ?
C31 N3 C32 118.1(2) . . ?
C8 C7 C6 105.8(2) . . ?
C8 C7 C9 125.9(2) . . ?
C6 C7 C9 128.1(2) . . ?
C26 C25 C30 114.3(2) . . ?
C26 C25 C24 120.8(2) . . ?
C30 C25 C24 124.8(2) . . ?
O1 C16 N2 122.0(2) . . ?
O1 C16 C8 120.2(2) . . ?
N2 C16 C8 117.7(2) . . ?
C18 C17 C22 119.5(3) . . ?
C18 C17 N2 119.3(2) . . ?
C22 C17 N2 121.1(2) . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 135.2(3) . . ?
C5 C6 C7 106.7(2) . . ?
C10 C9 C14 118.2(3) . . ?
C10 C9 C7 119.6(2) . . ?
C14 C9 C7 122.2(2) . . ?
N1 C8 C7 110.4(2) . . ?
N1 C8 C16 118.0(2) . . ?
C7 C8 C16 131.5(2) . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 C23 121.0(3) . . ?
C21 C20 C23 118.9(3) . . ?
C27 C26 C25 123.4(3) . . ?
C27 C26 H26 118.3 . . ?
C25 C26 H26 118.3 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C29 C30 C25 123.6(3) . . ?
C29 C30 N4 115.4(2) . . ?
C25 C30 N4 121.0(2) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C26 C27 C28 121.5(3) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
N1 C5 C4 129.4(3) . . ?
N1 C5 C6 108.0(2) . . ?
C4 C5 C6 122.5(3) . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N3 C28 C29 121.5(2) . . ?
N3 C28 C27 121.8(3) . . ?
C29 C28 C27 116.7(2) . . ?
C30 C29 C28 120.5(2) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 H1A 120.4 . . ?
C6 C1 H1A 120.4 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 C15 120.4(3) . . ?
C13 C12 C15 119.8(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N2 C24 C25 112.7(2) . . ?
N2 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
N2 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
F5 C23 F4 107.0(2) . . ?
F5 C23 F6 105.6(2) . . ?
F4 C23 F6 105.4(2) . . ?
F5 C23 C20 113.1(2) . . ?
F4 C23 C20 113.3(2) . . ?
F6 C23 C20 111.8(2) . . ?
C1 C2 C3 121.7(3) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
N3 C32 H32A 109.5 . . ?
N3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
F1 C15 F2 108.7(3) . . ?
F1 C15 F3 104.4(4) . . ?
F2 C15 F3 102.7(3) . . ?
F1 C15 C12 113.0(3) . . ?
F2 C15 C12 114.5(3) . . ?
F3 C15 C12 112.5(3) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

_refine_diff_density_max         1.251
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.069



####################################################################### 
# 
# 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_MAB_11_a
_database_code_depnum_ccdc_archive 'CCDC 2127607'
loop_
_audit_author_name
_audit_author_address
'Dr. Thangavel Vijayakanth'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2025-04-02 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            'C37 H25 F6 N3 O4'
_chemical_formula_weight         689.60

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'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.639(5)
_cell_length_b                   14.954(7)
_cell_length_c                   18.483(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.594(11)
_cell_angle_gamma                90
_cell_volume                     3181(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1350
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      17.83

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36708
_diffrn_reflns_av_unetI/netI     0.1859
_diffrn_reflns_av_R_equivalents  0.1464
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.114
_diffrn_reflns_theta_max         24.767
_diffrn_reflns_theta_full        24.767
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             10653
_reflns_number_gt                5535
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.953

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0627P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1664 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10653
_refine_ls_number_parameters     903
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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
F1 F 0.0689(5) -0.0252(4) 0.1564(3) 0.0354(16) Uani 1 1 d . . . . .
F2 F -0.0234(5) 0.0768(4) 0.0892(3) 0.0370(16) Uani 1 1 d . . . . .
F3 F 0.1644(5) 0.0675(4) 0.0988(3) 0.0411(17) Uani 1 1 d . . . . .
F4 F 0.0485(5) 0.3745(5) 0.0287(3) 0.051(2) Uani 1 1 d . . . . .
F5 F 0.1914(5) 0.3277(5) -0.0203(3) 0.052(2) Uani 1 1 d . . . . .
F6 F 0.1851(6) 0.4643(5) 0.0130(3) 0.057(2) Uani 1 1 d . . . . .
F7 F 0.8205(6) 0.3804(5) 0.1171(4) 0.066(2) Uani 1 1 d . . . . .
F8 F 0.9597(5) 0.4652(5) 0.1638(3) 0.0454(19) Uani 1 1 d . . . . .
F9 F 0.8371(6) 0.5102(6) 0.0740(3) 0.067(2) Uani 1 1 d . . . . .
F10 F 0.4313(6) 0.5133(6) -0.0086(4) 0.062(2) Uani 1 1 d . . . . .
F11 F 0.3199(6) 0.6250(5) -0.0388(3) 0.058(2) Uani 1 1 d . . . . .
F12 F 0.4882(6) 0.6188(5) -0.0739(3) 0.057(2) Uani 1 1 d . . . . .
O5 O 0.7015(5) 0.3760(5) 0.8723(3) 0.0274(18) Uani 1 1 d . . . . .
O4 O 0.2665(5) 0.3493(4) 0.4794(3) 0.0209(16) Uani 1 1 d . . . . .
O7 O 0.2567(5) 0.5103(4) 0.3859(3) 0.0213(16) Uani 1 1 d . . . . .
O8 O 0.5191(5) 0.7229(5) 0.4061(3) 0.0267(17) Uani 1 1 d . . . . .
O6 O 0.2211(5) 0.5528(5) 0.4927(3) 0.0251(18) Uani 1 1 d . . . . .
O3 O -0.0859(6) 0.4922(5) 0.4315(3) 0.0263(17) Uani 1 1 d . . . . .
O1 O -0.1222(6) 0.1520(5) 0.8835(3) 0.0310(19) Uani 1 1 d . . . . .
O2 O -0.0541(6) 0.5346(5) 0.5457(4) 0.0298(18) Uani 1 1 d . . . . .
N4 N 0.2895(7) 0.5303(5) 0.4504(4) 0.021(2) Uani 1 1 d . . . . .
N1 N -0.0547(6) 0.4787(6) 0.4973(5) 0.026(2) Uani 1 1 d . . . . .
N6 N 0.6902(6) 0.8336(6) 0.3600(4) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.6990 0.8349 0.4081 0.026 Uiso 1 1 calc R U . . .
N2 N 0.1518(6) 0.3048(5) 0.3756(4) 0.0169(19) Uani 1 1 d . . . . .
N5 N 0.5555(6) 0.6159(6) 0.3263(4) 0.019(2) Uani 1 1 d . . . . .
N3 N 0.4614(6) 0.2728(6) 0.4405(4) 0.021(2) Uani 1 1 d . . . . .
H3 H 0.4604 0.2696 0.4880 0.025 Uiso 1 1 calc R U . . .
C34 C 0.2233(8) 0.4182(7) 0.1629(5) 0.019(2) Uani 1 1 d . . . . .
H34 H 0.1851 0.4741 0.1539 0.023 Uiso 1 1 calc R U . . .
C61 C 0.6301(8) 0.7698(7) 0.3164(5) 0.019(2) Uani 1 1 d . . . . .
C10 C -0.0195(8) 0.3866(6) 0.5192(5) 0.017(2) Uani 1 1 d . . . . .
C33 C 0.2762(8) 0.3963(7) 0.2329(5) 0.020(2) Uani 1 1 d . . . . .
H33 H 0.2722 0.4370 0.2719 0.024 Uiso 1 1 calc R U . . .
C37 C 0.2261(8) 0.3584(7) 0.1063(5) 0.022(2) Uani 1 1 d . . . . .
C32 C 0.3354(8) 0.3154(7) 0.2470(5) 0.019(2) Uani 1 1 d . . . . .
C51 C 0.4136(7) 0.5253(6) 0.4789(5) 0.016(2) Uani 1 1 d . . . . .
C54 C 0.6299(8) 0.5769(7) 0.2796(5) 0.020(2) Uani 1 1 d . . . . .
C38 C 0.1653(9) 0.3812(8) 0.0327(5) 0.031(3) Uani 1 1 d . . . . .
C17 C 0.1758(8) 0.1575(7) 0.3233(5) 0.020(2) Uani 1 1 d . . . . .
H17 H 0.2222 0.1402 0.3678 0.024 Uiso 1 1 calc R U . . .
C45 C 0.5929(8) 0.4609(7) 0.6584(5) 0.020(2) Uani 1 1 d . . . . .
C69 C 0.5810(8) 0.7394(7) 0.1777(5) 0.020(2) Uani 1 1 d . . . . .
C62 C 0.6349(8) 0.7881(7) 0.2439(5) 0.021(2) Uani 1 1 d . . . . .
C19 C 0.1561(8) 0.0970(7) 0.2654(5) 0.022(2) Uani 1 1 d . . . . .
H19 H 0.1897 0.0390 0.2700 0.027 Uiso 1 1 calc R U . . .
C22 C 0.0736(9) 0.0611(8) 0.1367(5) 0.030(3) Uani 1 1 d . . . . .
C23 C 0.2593(8) 0.3154(7) 0.4174(5) 0.022(2) Uani 1 1 d . . . . .
C21 C 0.0866(8) 0.1226(7) 0.2007(5) 0.019(2) Uani 1 1 d . . . . .
C59 C 0.7737(8) 0.5022(7) 0.1888(5) 0.024(3) Uani 1 1 d . . . . .
C14 C 0.0560(7) 0.3589(7) 0.3981(5) 0.020(2) Uani 1 1 d . . . . .
H14A H -0.0135 0.3541 0.3602 0.025 Uiso 1 1 calc R U . . .
H14B H 0.0797 0.4225 0.4018 0.025 Uiso 1 1 calc R U . . .
C44 C 0.6741(8) 0.3919(7) 0.6763(5) 0.020(2) Uani 1 1 d . . . . .
H44 H 0.7059 0.3623 0.6384 0.024 Uiso 1 1 calc R U . . .
C70 C 0.4654(8) 0.7125(7) 0.1680(5) 0.023(3) Uani 1 1 d . . . . .
H70 H 0.4196 0.7243 0.2054 0.028 Uiso 1 1 calc R U . . .
C18 C 0.0566(8) 0.2670(7) 0.2521(5) 0.020(2) Uani 1 1 d . . . . .
H18 H 0.0220 0.3246 0.2473 0.024 Uiso 1 1 calc R U . . .
C46 C 0.5591(8) 0.4883(7) 0.5811(5) 0.021(2) Uani 1 1 d . . . . .
C16 C 0.1280(8) 0.2429(7) 0.3165(5) 0.019(2) Uani 1 1 d . . . . .
C27 C 0.5563(9) 0.2598(7) 0.4070(5) 0.024(2) Uani 1 1 d . . . . .
C74 C 0.4831(9) 0.6506(7) 0.0503(5) 0.023(3) Uani 1 1 d . . . . .
C13 C 0.0248(8) 0.3281(7) 0.4717(5) 0.018(2) Uani 1 1 d . . . . .
C6 C 0.0039(8) 0.2886(7) 0.7499(5) 0.020(2) Uani 1 1 d . . . . .
H6A H 0.0498 0.3407 0.7473 0.024 Uiso 1 1 calc R U . . .
C26 C 0.5224(8) 0.2724(7) 0.3308(5) 0.022(2) Uani 1 1 d . . . . .
C12 C 0.0449(7) 0.2413(7) 0.4953(5) 0.020(2) Uani 1 1 d . . . . .
H12 H 0.0753 0.1997 0.4642 0.024 Uiso 1 1 calc R U . . .
C8 C -0.0159(8) 0.2736(7) 0.6127(5) 0.021(2) Uani 1 1 d . . . . .
C24 C 0.3665(8) 0.2919(7) 0.3882(5) 0.024(3) Uani 1 1 d . . . . .
C55 C 0.7489(9) 0.5920(7) 0.2926(5) 0.026(3) Uani 1 1 d . . . . .
H55 H 0.7820 0.6269 0.3334 0.032 Uiso 1 1 calc R U . . .
C01O C 0.5672(8) 0.7016(7) 0.3529(5) 0.023(3) Uani 1 1 d . . . . .
C11 C 0.0219(8) 0.2132(7) 0.5633(5) 0.022(2) Uani 1 1 d . . . . .
H11 H 0.0320 0.1520 0.5766 0.026 Uiso 1 1 calc R U . . .
C5 C -0.0193(8) 0.2590(7) 0.8177(5) 0.020(2) Uani 1 1 d . . . . .
H5 H 0.0128 0.2893 0.8612 0.024 Uiso 1 1 calc R U . . .
C25 C 0.4016(8) 0.2939(7) 0.3195(5) 0.021(2) Uani 1 1 d . . . . .
C66 C 0.8304(9) 1.0243(7) 0.2787(5) 0.028(3) Uani 1 1 d . . . . .
H66 H 0.8768 1.0762 0.2896 0.034 Uiso 1 1 calc R U . . .
C40 C 0.6600(8) 0.4091(7) 0.8035(5) 0.024(3) Uani 1 1 d . . . . .
C42 C 0.7085(8) 0.3664(7) 0.7479(5) 0.024(3) Uani 1 1 d . . . . .
H42 H 0.7644 0.3203 0.7593 0.028 Uiso 1 1 calc R U . . .
C36 C 0.2831(9) 0.2770(7) 0.1184(5) 0.028(3) Uani 1 1 d . . . . .
H36 H 0.2849 0.2361 0.0793 0.033 Uiso 1 1 calc R U . . .
C9 C -0.0367(7) 0.3603(7) 0.5898(5) 0.019(2) Uani 1 1 d . . . . .
H9 H -0.0629 0.4028 0.6219 0.023 Uiso 1 1 calc R U . . .
C64 C 0.7353(8) 0.8964(7) 0.3158(5) 0.021(2) Uani 1 1 d . . . . .
C7 C -0.0389(8) 0.2431(7) 0.6859(5) 0.023(2) Uani 1 1 d . . . . .
C52 C 0.4635(8) 0.5620(7) 0.3516(5) 0.020(2) Uani 1 1 d . . . . .
H52A H 0.4493 0.5080 0.3206 0.024 Uiso 1 1 calc R U . . .
H52B H 0.3906 0.5972 0.3461 0.024 Uiso 1 1 calc R U . . .
C65 C 0.7999(8) 0.9727(7) 0.3350(5) 0.024(2) Uani 1 1 d . . . . .
H65 H 0.8223 0.9891 0.3847 0.029 Uiso 1 1 calc R U . . .
C2 C -0.0899(8) 0.1847(7) 0.8208(5) 0.025(3) Uani 1 1 d . . . . .
C43 C 0.5449(8) 0.5011(7) 0.7148(5) 0.025(3) Uani 1 1 d . . . . .
H43 H 0.4891 0.5473 0.7037 0.030 Uiso 1 1 calc R U . . .
C100 C 0.4955(8) 0.5342(7) 0.4305(5) 0.023(3) Uani 1 1 d . . . . .
C28 C 0.6714(8) 0.2379(7) 0.4371(6) 0.031(3) Uani 1 1 d . . . . .
H28 H 0.6932 0.2287 0.4882 0.037 Uiso 1 1 calc R U . . .
C71 C 0.4153(8) 0.6686(7) 0.1044(5) 0.026(3) Uani 1 1 d . . . . .
H71 H 0.3359 0.6512 0.0982 0.031 Uiso 1 1 calc R U . . .
C30 C 0.7195(9) 0.2453(7) 0.3129(6) 0.031(3) Uani 1 1 d . . . . .
H30 H 0.7768 0.2412 0.2815 0.038 Uiso 1 1 calc R U . . .
C4 C -0.1057(8) 0.1668(7) 0.6901(5) 0.024(3) Uani 1 1 d . . . . .
H4 H -0.1334 0.1337 0.6471 0.029 Uiso 1 1 calc R U . . .
C58 C 0.6535(8) 0.4840(7) 0.1759(5) 0.028(3) Uani 1 1 d . . . . .
H58 H 0.6215 0.4466 0.1365 0.033 Uiso 1 1 calc R U . . .
C63 C 0.7002(8) 0.8697(7) 0.2424(5) 0.021(2) Uani 1 1 d . . . . .
C72 C 0.6474(8) 0.7177(7) 0.1227(5) 0.024(3) Uani 1 1 d . . . . .
H72 H 0.7273 0.7337 0.1288 0.029 Uiso 1 1 calc R U . . .
C56 C 0.8196(9) 0.5555(7) 0.2455(5) 0.026(3) Uani 1 1 d . . . . .
H56 H 0.9005 0.5680 0.2531 0.031 Uiso 1 1 calc R U . . .
C47 C 0.4438(8) 0.5050(7) 0.5526(5) 0.023(2) Uani 1 1 d . . . . .
H47 H 0.3856 0.5026 0.5835 0.028 Uiso 1 1 calc R U . . .
C68 C 0.7283(8) 0.9248(7) 0.1861(5) 0.023(3) Uani 1 1 d . . . . .
H68 H 0.7032 0.9103 0.1362 0.027 Uiso 1 1 calc R U . . .
C41 C 0.5776(8) 0.4745(7) 0.7877(5) 0.026(3) Uani 1 1 d . . . . .
H41 H 0.5431 0.5015 0.8257 0.031 Uiso 1 1 calc R U . . .
C48 C 0.6408(8) 0.4943(7) 0.5340(5) 0.025(3) Uani 1 1 d . . . . .
H48 H 0.7199 0.4817 0.5520 0.030 Uiso 1 1 calc R U . . .
C31 C 0.6075(8) 0.2656(7) 0.2842(6) 0.028(3) Uani 1 1 d . . . . .
H31 H 0.5871 0.2751 0.2330 0.034 Uiso 1 1 calc R U . . .
C57 C 0.5828(8) 0.5219(7) 0.2218(5) 0.022(2) Uani 1 1 d . . . . .
H57 H 0.5017 0.5103 0.2138 0.027 Uiso 1 1 calc R U . . .
C67 C 0.7929(8) 1.0001(7) 0.2052(5) 0.028(3) Uani 1 1 d . . . . .
H67 H 0.8132 1.0375 0.1675 0.033 Uiso 1 1 calc R U . . .
C73 C 0.5995(9) 0.6741(7) 0.0607(5) 0.029(3) Uani 1 1 d . . . . .
H73 H 0.6463 0.6598 0.0244 0.035 Uiso 1 1 calc R U . . .
C49 C 0.6103(8) 0.5183(7) 0.4611(5) 0.024(2) Uani 1 1 d . . . . .
H49 H 0.6696 0.5240 0.4312 0.029 Uiso 1 1 calc R U . . .
C35 C 0.3378(8) 0.2559(7) 0.1888(5) 0.026(3) Uani 1 1 d . . . . .
H35 H 0.3771 0.2004 0.1973 0.032 Uiso 1 1 calc R U . . .
C20 C 0.0365(8) 0.2058(7) 0.1949(5) 0.023(3) Uani 1 1 d . . . . .
H20 H -0.0128 0.2219 0.1511 0.027 Uiso 1 1 calc R U . . .
C3 C -0.1318(8) 0.1393(7) 0.7578(5) 0.029(3) Uani 1 1 d . . . . .
H3A H -0.1795 0.0881 0.7605 0.035 Uiso 1 1 calc R U . . .
C60 C 0.8465(10) 0.4653(9) 0.1370(6) 0.040(3) Uani 1 1 d . . . . .
C29 C 0.7513(8) 0.2304(8) 0.3887(6) 0.037(3) Uani 1 1 d . . . . .
H29 H 0.8294 0.2148 0.4070 0.045 Uiso 1 1 calc R U . . .
C75 C 0.4312(10) 0.6026(10) -0.0165(6) 0.041(3) Uani 1 1 d . . . . .
C1 C -0.0877(9) 0.2012(8) 0.9500(5) 0.040(3) Uani 1 1 d . . . . .
H1A H -0.0029 0.1995 0.9627 0.060 Uiso 1 1 calc R U . . .
H1B H -0.1233 0.1743 0.9896 0.060 Uiso 1 1 calc R U . . .
H1C H -0.1134 0.2634 0.9430 0.060 Uiso 1 1 calc R U . . .
C39 C 0.6421(9) 0.4074(8) 0.9310(5) 0.036(3) Uani 1 1 d . . . . .
H39A H 0.6538 0.4720 0.9372 0.053 Uiso 1 1 calc R U . . .
H39B H 0.6735 0.3767 0.9765 0.053 Uiso 1 1 calc R U . . .
H39C H 0.5588 0.3947 0.9189 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C22 1.343(12) . ?
F2 C22 1.343(11) . ?
F3 C22 1.355(11) . ?
F4 C38 1.355(11) . ?
F5 C38 1.334(11) . ?
F6 C38 1.325(12) . ?
F7 C60 1.343(14) . ?
F8 C60 1.337(12) . ?
F9 C60 1.334(13) . ?
F10 C75 1.343(14) . ?
F11 C75 1.342(12) . ?
F12 C75 1.355(12) . ?
O5 C40 1.382(11) . ?
O5 C39 1.448(10) . ?
O4 C23 1.245(10) . ?
O7 N4 1.234(9) . ?
O8 C01O 1.243(10) . ?
O6 N4 1.242(9) . ?
O3 N1 1.231(9) . ?
O1 C2 1.362(10) . ?
O1 C1 1.437(11) . ?
O2 N1 1.224(10) . ?
N4 C51 1.463(11) . ?
N1 C10 1.476(12) . ?
N6 C61 1.373(12) . ?
N6 C64 1.398(11) . ?
N6 H6 0.8800 . ?
N2 C23 1.377(11) . ?
N2 C16 1.426(11) . ?
N2 C14 1.487(11) . ?
N5 C01O 1.372(12) . ?
N5 C54 1.434(11) . ?
N5 C52 1.471(11) . ?
N3 C27 1.359(11) . ?
N3 C24 1.384(11) . ?
N3 H3 0.8800 . ?
C34 C37 1.380(12) . ?
C34 C33 1.387(12) . ?
C34 H34 0.9500 . ?
C61 C62 1.377(12) . ?
C61 C01O 1.477(13) . ?
C10 C13 1.392(12) . ?
C10 C9 1.406(11) . ?
C33 C32 1.397(13) . ?
C33 H33 0.9500 . ?
C37 C36 1.388(14) . ?
C37 C38 1.476(13) . ?
C32 C35 1.399(13) . ?
C32 C25 1.479(13) . ?
C51 C47 1.388(11) . ?
C51 C100 1.408(12) . ?
C54 C55 1.389(13) . ?
C54 C57 1.393(13) . ?
C17 C16 1.390(14) . ?
C17 C19 1.394(13) . ?
C17 H17 0.9500 . ?
C45 C43 1.391(12) . ?
C45 C44 1.404(13) . ?
C45 C46 1.481(12) . ?
C69 C70 1.390(12) . ?
C69 C72 1.405(11) . ?
C69 C62 1.480(13) . ?
C62 C63 1.440(13) . ?
C19 C21 1.393(12) . ?
C19 H19 0.9500 . ?
C22 C21 1.489(13) . ?
C23 C24 1.474(13) . ?
C21 C20 1.372(14) . ?
C59 C56 1.361(13) . ?
C59 C58 1.410(13) . ?
C59 C60 1.477(13) . ?
C14 C13 1.531(12) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C44 C42 1.377(12) . ?
C44 H44 0.9500 . ?
C70 C71 1.396(12) . ?
C70 H70 0.9500 . ?
C18 C20 1.392(13) . ?
C18 C16 1.394(12) . ?
C18 H18 0.9500 . ?
C46 C48 1.386(12) . ?
C46 C47 1.389(12) . ?
C27 C28 1.410(13) . ?
C27 C26 1.417(12) . ?
C74 C73 1.385(13) . ?
C74 C71 1.391(12) . ?
C74 C75 1.476(14) . ?
C13 C12 1.377(13) . ?
C6 C7 1.392(13) . ?
C6 C5 1.392(11) . ?
C6 H6A 0.9500 . ?
C26 C31 1.410(12) . ?
C26 C25 1.427(12) . ?
C12 C11 1.390(12) . ?
C12 H12 0.9500 . ?
C8 C9 1.375(13) . ?
C8 C11 1.400(13) . ?
C8 C7 1.490(12) . ?
C24 C25 1.391(12) . ?
C55 C56 1.394(12) . ?
C55 H55 0.9500 . ?
C11 H11 0.9500 . ?
C5 C2 1.390(13) . ?
C5 H5 0.9500 . ?
C66 C65 1.383(13) . ?
C66 C67 1.411(13) . ?
C66 H66 0.9500 . ?
C40 C41 1.370(13) . ?
C40 C42 1.400(12) . ?
C42 H42 0.9500 . ?
C36 C35 1.396(13) . ?
C36 H36 0.9500 . ?
C9 H9 0.9500 . ?
C64 C65 1.383(14) . ?
C64 C63 1.415(12) . ?
C7 C4 1.389(14) . ?
C52 C100 1.508(12) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C65 H65 0.9500 . ?
C2 C3 1.373(13) . ?
C43 C41 1.402(12) . ?
C43 H43 0.9500 . ?
C100 C49 1.391(13) . ?
C28 C29 1.389(13) . ?
C28 H28 0.9500 . ?
C71 H71 0.9500 . ?
C30 C31 1.366(13) . ?
C30 C29 1.411(13) . ?
C30 H30 0.9500 . ?
C4 C3 1.395(12) . ?
C4 H4 0.9500 . ?
C58 C57 1.388(12) . ?
C58 H58 0.9500 . ?
C63 C68 1.403(12) . ?
C72 C73 1.363(12) . ?
C72 H72 0.9500 . ?
C56 H56 0.9500 . ?
C47 H47 0.9500 . ?
C68 C67 1.372(14) . ?
C68 H68 0.9500 . ?
C41 H41 0.9500 . ?
C48 C49 1.388(12) . ?
C48 H48 0.9500 . ?
C31 H31 0.9500 . ?
C57 H57 0.9500 . ?
C67 H67 0.9500 . ?
C73 H73 0.9500 . ?
C49 H49 0.9500 . ?
C35 H35 0.9500 . ?
C20 H20 0.9500 . ?
C3 H3A 0.9500 . ?
C29 H29 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

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
C40 O5 C39 115.6(8) . . ?
C2 O1 C1 117.8(8) . . ?
O7 N4 O6 122.6(8) . . ?
O7 N4 C51 118.7(7) . . ?
O6 N4 C51 118.7(8) . . ?
O2 N1 O3 125.4(9) . . ?
O2 N1 C10 117.7(8) . . ?
O3 N1 C10 116.9(8) . . ?
C61 N6 C64 109.0(7) . . ?
C61 N6 H6 125.5 . . ?
C64 N6 H6 125.5 . . ?
C23 N2 C16 124.1(8) . . ?
C23 N2 C14 115.8(7) . . ?
C16 N2 C14 120.0(7) . . ?
C01O N5 C54 124.0(8) . . ?
C01O N5 C52 115.8(8) . . ?
C54 N5 C52 120.1(8) . . ?
C27 N3 C24 109.2(7) . . ?
C27 N3 H3 125.4 . . ?
C24 N3 H3 125.4 . . ?
C37 C34 C33 119.8(9) . . ?
C37 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
N6 C61 C62 110.0(9) . . ?
N6 C61 C01O 117.1(8) . . ?
C62 C61 C01O 132.7(9) . . ?
C13 C10 C9 121.8(9) . . ?
C13 C10 N1 121.8(8) . . ?
C9 C10 N1 116.3(8) . . ?
C34 C33 C32 121.1(9) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C34 C37 C36 120.7(9) . . ?
C34 C37 C38 119.1(9) . . ?
C36 C37 C38 120.2(9) . . ?
C33 C32 C35 118.2(9) . . ?
C33 C32 C25 122.2(9) . . ?
C35 C32 C25 119.4(9) . . ?
C47 C51 C100 123.2(9) . . ?
C47 C51 N4 117.1(8) . . ?
C100 C51 N4 119.5(8) . . ?
C55 C54 C57 119.8(9) . . ?
C55 C54 N5 120.4(9) . . ?
C57 C54 N5 119.9(9) . . ?
F6 C38 F5 107.0(8) . . ?
F6 C38 F4 105.6(9) . . ?
F5 C38 F4 104.6(8) . . ?
F6 C38 C37 113.0(9) . . ?
F5 C38 C37 114.1(9) . . ?
F4 C38 C37 111.9(8) . . ?
C16 C17 C19 120.6(9) . . ?
C16 C17 H17 119.7 . . ?
C19 C17 H17 119.7 . . ?
C43 C45 C44 118.1(9) . . ?
C43 C45 C46 121.6(9) . . ?
C44 C45 C46 120.3(8) . . ?
C70 C69 C72 117.8(9) . . ?
C70 C69 C62 122.1(8) . . ?
C72 C69 C62 120.1(8) . . ?
C61 C62 C63 106.6(8) . . ?
C61 C62 C69 129.2(9) . . ?
C63 C62 C69 124.1(8) . . ?
C21 C19 C17 119.3(9) . . ?
C21 C19 H19 120.4 . . ?
C17 C19 H19 120.4 . . ?
F1 C22 F2 106.3(9) . . ?
F1 C22 F3 106.0(8) . . ?
F2 C22 F3 107.1(8) . . ?
F1 C22 C21 112.4(8) . . ?
F2 C22 C21 112.7(9) . . ?
F3 C22 C21 111.9(9) . . ?
O4 C23 N2 119.6(8) . . ?
O4 C23 C24 119.3(9) . . ?
N2 C23 C24 121.0(8) . . ?
C20 C21 C19 120.1(9) . . ?
C20 C21 C22 120.5(9) . . ?
C19 C21 C22 119.3(9) . . ?
C56 C59 C58 120.5(9) . . ?
C56 C59 C60 121.5(10) . . ?
C58 C59 C60 117.9(9) . . ?
N2 C14 C13 111.9(8) . . ?
N2 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C42 C44 C45 121.3(9) . . ?
C42 C44 H44 119.3 . . ?
C45 C44 H44 119.3 . . ?
C69 C70 C71 121.3(8) . . ?
C69 C70 H70 119.3 . . ?
C71 C70 H70 119.3 . . ?
C20 C18 C16 119.4(10) . . ?
C20 C18 H18 120.3 . . ?
C16 C18 H18 120.3 . . ?
C48 C46 C47 117.7(8) . . ?
C48 C46 C45 121.0(8) . . ?
C47 C46 C45 121.2(8) . . ?
C17 C16 C18 119.5(9) . . ?
C17 C16 N2 119.9(8) . . ?
C18 C16 N2 120.6(9) . . ?
N3 C27 C28 129.9(9) . . ?
N3 C27 C26 108.0(8) . . ?
C28 C27 C26 122.0(9) . . ?
C73 C74 C71 120.0(9) . . ?
C73 C74 C75 120.6(9) . . ?
C71 C74 C75 119.3(9) . . ?
C12 C13 C10 117.0(8) . . ?
C12 C13 C14 120.9(8) . . ?
C10 C13 C14 122.0(9) . . ?
C7 C6 C5 121.1(9) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C31 C26 C27 118.8(9) . . ?
C31 C26 C25 133.9(9) . . ?
C27 C26 C25 107.3(8) . . ?
C13 C12 C11 121.7(9) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C9 C8 C11 117.8(8) . . ?
C9 C8 C7 121.4(9) . . ?
C11 C8 C7 120.7(9) . . ?
N3 C24 C25 109.2(8) . . ?
N3 C24 C23 115.1(8) . . ?
C25 C24 C23 135.1(9) . . ?
C54 C55 C56 119.6(9) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
O8 C01O N5 119.4(9) . . ?
O8 C01O C61 119.8(9) . . ?
N5 C01O C61 120.6(8) . . ?
C12 C11 C8 121.0(10) . . ?
C12 C11 H11 119.5 . . ?
C8 C11 H11 119.5 . . ?
C2 C5 C6 119.2(9) . . ?
C2 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C24 C25 C26 106.2(8) . . ?
C24 C25 C32 130.4(8) . . ?
C26 C25 C32 123.3(8) . . ?
C65 C66 C67 120.2(10) . . ?
C65 C66 H66 119.9 . . ?
C67 C66 H66 119.9 . . ?
C41 C40 O5 126.1(9) . . ?
C41 C40 C42 121.0(9) . . ?
O5 C40 C42 112.9(9) . . ?
C44 C42 C40 119.2(10) . . ?
C44 C42 H42 120.4 . . ?
C40 C42 H42 120.4 . . ?
C37 C36 C35 119.3(9) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C8 C9 C10 120.4(9) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C65 C64 N6 129.9(9) . . ?
C65 C64 C63 123.2(9) . . ?
N6 C64 C63 107.0(9) . . ?
C4 C7 C6 119.1(9) . . ?
C4 C7 C8 118.7(9) . . ?
C6 C7 C8 122.2(9) . . ?
N5 C52 C100 111.9(7) . . ?
N5 C52 H52A 109.2 . . ?
C100 C52 H52A 109.2 . . ?
N5 C52 H52B 109.2 . . ?
C100 C52 H52B 109.2 . . ?
H52A C52 H52B 107.9 . . ?
C66 C65 C64 117.3(9) . . ?
C66 C65 H65 121.4 . . ?
C64 C65 H65 121.4 . . ?
O1 C2 C3 115.9(9) . . ?
O1 C2 C5 124.3(9) . . ?
C3 C2 C5 119.9(9) . . ?
C45 C43 C41 121.1(10) . . ?
C45 C43 H43 119.5 . . ?
C41 C43 H43 119.5 . . ?
C49 C100 C51 115.1(9) . . ?
C49 C100 C52 121.6(8) . . ?
C51 C100 C52 123.2(9) . . ?
C29 C28 C27 116.9(10) . . ?
C29 C28 H28 121.6 . . ?
C27 C28 H28 121.6 . . ?
C74 C71 C70 119.1(9) . . ?
C74 C71 H71 120.5 . . ?
C70 C71 H71 120.5 . . ?
C31 C30 C29 121.0(9) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C7 C4 C3 119.4(10) . . ?
C7 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C57 C58 C59 118.8(9) . . ?
C57 C58 H58 120.6 . . ?
C59 C58 H58 120.6 . . ?
C68 C63 C64 118.6(9) . . ?
C68 C63 C62 133.9(9) . . ?
C64 C63 C62 107.4(8) . . ?
C73 C72 C69 121.3(9) . . ?
C73 C72 H72 119.4 . . ?
C69 C72 H72 119.4 . . ?
C59 C56 C55 120.7(9) . . ?
C59 C56 H56 119.7 . . ?
C55 C56 H56 119.7 . . ?
C51 C47 C46 120.0(8) . . ?
C51 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C67 C68 C63 118.1(9) . . ?
C67 C68 H68 120.9 . . ?
C63 C68 H68 120.9 . . ?
C40 C41 C43 119.2(9) . . ?
C40 C41 H41 120.4 . . ?
C43 C41 H41 120.4 . . ?
C46 C48 C49 121.8(9) . . ?
C46 C48 H48 119.1 . . ?
C49 C48 H48 119.1 . . ?
C30 C31 C26 119.6(9) . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?
C58 C57 C54 120.6(9) . . ?
C58 C57 H57 119.7 . . ?
C54 C57 H57 119.7 . . ?
C68 C67 C66 122.5(9) . . ?
C68 C67 H67 118.7 . . ?
C66 C67 H67 118.7 . . ?
C72 C73 C74 120.5(9) . . ?
C72 C73 H73 119.8 . . ?
C74 C73 H73 119.8 . . ?
C48 C49 C100 122.1(9) . . ?
C48 C49 H49 119.0 . . ?
C100 C49 H49 119.0 . . ?
C36 C35 C32 120.9(10) . . ?
C36 C35 H35 119.5 . . ?
C32 C35 H35 119.5 . . ?
C21 C20 C18 121.0(9) . . ?
C21 C20 H20 119.5 . . ?
C18 C20 H20 119.5 . . ?
C2 C3 C4 121.2(10) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
F9 C60 F8 105.8(10) . . ?
F9 C60 F7 104.5(9) . . ?
F8 C60 F7 105.6(9) . . ?
F9 C60 C59 113.4(10) . . ?
F8 C60 C59 112.9(9) . . ?
F7 C60 C59 113.8(10) . . ?
C28 C29 C30 121.7(10) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
F11 C75 F10 105.4(10) . . ?
F11 C75 F12 106.2(9) . . ?
F10 C75 F12 105.7(10) . . ?
F11 C75 C74 113.1(10) . . ?
F10 C75 C74 113.5(10) . . ?
F12 C75 C74 112.4(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5 C39 H39A 109.5 . . ?
O5 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O5 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.080



