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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 2293492'
loop_
_audit_author_name
_audit_author_address
JiangYonggang
;yunnandaxue
China
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2023-09-05
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C32 H27 F2 N3 O'
_chemical_formula_moiety         'C32 H27 F2 N3 O'
_chemical_formula_weight         507.56
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C2(H2), C28(H28), C19(H19), C17(H17), C29(H29), C22(H22), C15(H15),
 C31(H31), C24(H24), C26(H26), C30(H30), C25(H25), C5(H5), C4(H4), C23(H23),
 C3(H3)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.9152(16)
_cell_length_b                   9.8681(9)
_cell_length_c                   18.7455(19)
_cell_angle_alpha                90
_cell_angle_beta                 111.468(4)
_cell_angle_gamma                90
_cell_volume                     2567.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    6070
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.16
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5380
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.7215.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            16313
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             5799
_reflns_number_gt                4877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.812
_reflns_Friedel_fraction_full    0.913
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0525P)²+0.0218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5799
_refine_ls_number_parameters     345
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.22845(15) 0.77340(19) 0.27544(11) 0.0327(5) Uani 1 1 d . . . . .
F2 F 0.43078(15) 1.15401(18) 0.32447(11) 0.0303(5) Uani 1 1 d . . . . .
O1 O 0.63519(17) 0.4351(2) 0.65102(13) 0.0237(5) Uani 1 1 d . . . . .
N3 N 0.45393(18) 0.7071(3) 0.54378(14) 0.0176(5) Uani 1 1 d . . . . .
N1 N 0.58519(19) 0.4614(3) 0.52056(14) 0.0195(6) Uani 1 1 d . . . . .
N2 N 0.6216(2) 0.5609(3) 0.41437(15) 0.0232(6) Uani 1 1 d . . . . .
C20 C 0.4262(2) 0.7576(3) 0.59497(16) 0.0161(6) Uani 1 1 d . . . . .
C27 C 0.3721(2) 0.6706(3) 0.63046(16) 0.0154(6) Uani 1 1 d . . . . .
C10 C 0.6243(2) 0.5047(3) 0.59428(17) 0.0185(6) Uani 1 1 d . . . . .
C32 C 0.3950(2) 0.5338(3) 0.64641(18) 0.0212(6) Uani 1 1 d . . . . .
H32 H 0.445149 0.493858 0.633663 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7095(2) 0.8913(3) 0.49122(18) 0.0222(7) Uani 1 1 d . . . . .
H2 H 0.704793 0.948070 0.530642 0.027 Uiso 1 1 calc R U . . .
C18 C 0.3103(2) 0.8401(3) 0.31961(18) 0.0232(7) Uani 1 1 d . . . . .
C28 C 0.2974(2) 0.7260(3) 0.64856(18) 0.0223(7) Uani 1 1 d . . . . .
H28 H 0.282149 0.819306 0.638643 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4103(3) 1.0283(3) 0.34362(18) 0.0227(7) Uani 1 1 d . . . . .
C14 C 0.4490(2) 0.8471(3) 0.43479(17) 0.0176(6) Uani 1 1 d . . . . .
C1 C 0.6607(2) 0.7690(3) 0.47488(17) 0.0198(6) Uani 1 1 d . . . . .
C19 C 0.3669(2) 0.7794(3) 0.38723(17) 0.0200(6) Uani 1 1 d . . . . .
H19 H 0.350306 0.693032 0.401181 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6534(2) 0.6515(3) 0.59432(17) 0.0186(6) Uani 1 1 d . . . . .
H9A H 0.723859 0.659383 0.607607 0.022 Uiso 1 1 calc R U . . .
H9B H 0.635137 0.704567 0.631716 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3289(3) 0.9639(3) 0.29482(18) 0.0244(7) Uani 1 1 d . . . . .
H17 H 0.288587 1.002567 0.247519 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5654(2) 0.5691(3) 0.46425(17) 0.0194(6) Uani 1 1 d . . . . .
H8 H 0.494955 0.573013 0.432770 0.023 Uiso 1 1 calc R U . . .
C21 C 0.4450(2) 0.9014(3) 0.62356(18) 0.0188(6) Uani 1 1 d . . . . .
C29 C 0.2448(3) 0.6479(3) 0.68083(19) 0.0244(7) Uani 1 1 d . . . . .
H29 H 0.192868 0.686784 0.691599 0.029 Uiso 1 1 calc R U . . .
C22 C 0.3998(2) 1.0105(3) 0.57782(19) 0.0239(7) Uani 1 1 d . . . . .
H22 H 0.353308 0.995106 0.527985 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5119(2) 0.7910(3) 0.51221(16) 0.0166(6) Uani 1 1 d . . . . .
H13 H 0.538228 0.869032 0.547758 0.020 Uiso 1 1 calc R U . . .
C15 C 0.4709(2) 0.9741(3) 0.41251(18) 0.0204(7) Uani 1 1 d . . . . .
H15 H 0.526423 1.022326 0.444031 0.024 Uiso 1 1 calc R U . . .
C31 C 0.3445(2) 0.4565(3) 0.68090(19) 0.0238(7) Uani 1 1 d . . . . .
H31 H 0.361723 0.364431 0.693466 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5984(2) 0.7022(3) 0.51193(16) 0.0174(6) Uani 1 1 d . . . . .
C24 C 0.4907(3) 1.1639(3) 0.6776(2) 0.0309(8) Uani 1 1 d . . . . .
H24 H 0.507717 1.253808 0.695583 0.037 Uiso 1 1 calc R U . . .
C26 C 0.5111(2) 0.9236(3) 0.69775(19) 0.0229(7) Uani 1 1 d . . . . .
H26 H 0.540180 0.849112 0.730021 0.028 Uiso 1 1 calc R U . . .
C30 C 0.2684(2) 0.5131(3) 0.69719(18) 0.0239(7) Uani 1 1 d . . . . .
H30 H 0.232933 0.459082 0.719533 0.029 Uiso 1 1 calc R U . . .
C25 C 0.5340(3) 1.0560(3) 0.7241(2) 0.0291(8) Uani 1 1 d . . . . .
H25 H 0.579604 1.071853 0.774195 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6695(2) 0.6847(3) 0.41782(18) 0.0217(7) Uani 1 1 d . . . . .
C5 C 0.7227(3) 0.7244(4) 0.37423(19) 0.0271(7) Uani 1 1 d . . . . .
H5 H 0.725953 0.668990 0.333814 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7711(3) 0.8480(4) 0.3914(2) 0.0292(8) Uani 1 1 d . . . . .
H4 H 0.808857 0.876134 0.362802 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5525(3) 0.3240(3) 0.4993(2) 0.0285(8) Uani 1 1 d . . . . .
H11A H 0.589015 0.283644 0.470524 0.043 Uiso 1 1 calc R U . . .
H11B H 0.483802 0.324683 0.467309 0.043 Uiso 1 1 calc R U . . .
H11C H 0.562624 0.270503 0.545655 0.043 Uiso 1 1 calc R U . . .
C23 C 0.4224(3) 1.1423(3) 0.6047(2) 0.0299(8) Uani 1 1 d . . . . .
H23 H 0.391388 1.217045 0.573517 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7655(2) 0.9305(4) 0.44927(19) 0.0279(8) Uani 1 1 d . . . . .
H3 H 0.799744 1.013776 0.460455 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5777(3) 0.4919(4) 0.3409(2) 0.0388(9) Uani 1 1 d . . . . .
H12A H 0.562065 0.398422 0.349610 0.058 Uiso 1 1 calc R U . . .
H12B H 0.622888 0.491563 0.313882 0.058 Uiso 1 1 calc R U . . .
H12C H 0.518603 0.539474 0.309768 0.058 Uiso 1 1 calc R U . . .


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 C18 1.367(4) . ?
F2 C16 1.357(4) . ?
O1 C10 1.226(4) . ?
N3 C20 1.277(4) . ?
N3 C13 1.469(4) . ?
N1 C10 1.358(4) . ?
N1 C8 1.451(4) . ?
N1 C11 1.446(4) . ?
N2 C8 1.468(4) . ?
N2 C6 1.404(4) . ?
N2 C12 1.459(4) . ?
C20 C27 1.491(4) . ?
C20 C21 1.507(4) . ?
C27 C32 1.397(4) . ?
C27 C28 1.390(4) . ?
C10 C9 1.512(4) . ?
C32 H32 0.9500 . ?
C32 C31 1.388(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(4) . ?
C2 C3 1.395(5) . ?
C18 C19 1.377(4) . ?
C18 C17 1.371(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(5) . ?
C16 C17 1.379(5) . ?
C16 C15 1.385(4) . ?
C14 C19 1.394(4) . ?
C14 C13 1.515(4) . ?
C14 C15 1.397(4) . ?
C1 C7 1.501(4) . ?
C1 C6 1.399(5) . ?
C19 H19 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C7 1.543(4) . ?
C17 H17 0.9500 . ?
C8 H8 1.0000 . ?
C8 C7 1.563(4) . ?
C21 C22 1.388(4) . ?
C21 C26 1.396(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(5) . ?
C13 H13 1.0000 . ?
C13 C7 1.560(4) . ?
C15 H15 0.9500 . ?
C31 H31 0.9500 . ?
C31 C30 1.395(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(5) . ?
C24 C23 1.390(6) . ?
C26 H26 0.9500 . ?
C26 C25 1.394(5) . ?
C30 H30 0.9500 . ?
C25 H25 0.9500 . ?
C6 C5 1.387(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C23 H23 0.9500 . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C20 N3 C13 118.9(2) . . ?
C10 N1 C8 114.0(2) . . ?
C10 N1 C11 123.5(3) . . ?
C11 N1 C8 121.9(2) . . ?
C6 N2 C8 108.8(2) . . ?
C6 N2 C12 119.6(3) . . ?
C12 N2 C8 117.6(3) . . ?
N3 C20 C27 119.2(3) . . ?
N3 C20 C21 124.4(3) . . ?
C27 C20 C21 116.4(3) . . ?
C32 C27 C20 121.5(3) . . ?
C28 C27 C20 119.7(3) . . ?
C28 C27 C32 118.9(3) . . ?
O1 C10 N1 125.3(3) . . ?
O1 C10 C9 126.1(3) . . ?
N1 C10 C9 108.6(3) . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 119.9(3) . . ?
C31 C32 H32 120.0 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
F1 C18 C19 117.3(3) . . ?
F1 C18 C17 118.0(3) . . ?
C17 C18 C19 124.6(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.4 . . ?
F2 C16 C17 118.3(3) . . ?
F2 C16 C15 117.8(3) . . ?
C17 C16 C15 123.8(3) . . ?
C19 C14 C13 121.9(3) . . ?
C19 C14 C15 119.1(3) . . ?
C15 C14 C13 118.9(3) . . ?
C2 C1 C7 130.1(3) . . ?
C2 C1 C6 120.0(3) . . ?
C6 C1 C7 109.9(3) . . ?
C18 C19 C14 118.6(3) . . ?
C18 C19 H19 120.7 . . ?
C14 C19 H19 120.7 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C10 C9 C7 105.2(2) . . ?
H9A C9 H9B 108.8 . . ?
C7 C9 H9A 110.7 . . ?
C7 C9 H9B 110.7 . . ?
C18 C17 C16 115.1(3) . . ?
C18 C17 H17 122.5 . . ?
C16 C17 H17 122.5 . . ?
N1 C8 N2 114.3(3) . . ?
N1 C8 H8 110.3 . . ?
N1 C8 C7 105.2(2) . . ?
N2 C8 H8 110.3 . . ?
N2 C8 C7 106.1(3) . . ?
C7 C8 H8 110.3 . . ?
C22 C21 C20 121.7(3) . . ?
C22 C21 C26 120.0(3) . . ?
C26 C21 C20 118.3(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 C28 119.5(3) . . ?
C30 C29 H29 120.2 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
N3 C13 C14 110.0(2) . . ?
N3 C13 H13 108.1 . . ?
N3 C13 C7 107.1(2) . . ?
C14 C13 H13 108.1 . . ?
C14 C13 C7 115.1(2) . . ?
C7 C13 H13 108.1 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C32 C31 H31 119.8 . . ?
C32 C31 C30 120.4(3) . . ?
C30 C31 H31 119.8 . . ?
C1 C7 C9 114.3(3) . . ?
C1 C7 C8 102.9(2) . . ?
C1 C7 C13 114.1(2) . . ?
C9 C7 C8 103.9(2) . . ?
C9 C7 C13 108.4(2) . . ?
C13 C7 C8 112.7(2) . . ?
C25 C24 H24 119.7 . . ?
C25 C24 C23 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C21 C26 H26 120.3 . . ?
C25 C26 C21 119.5(3) . . ?
C25 C26 H26 120.3 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C1 C6 N2 111.3(3) . . ?
C5 C6 N2 127.6(3) . . ?
C5 C6 C1 121.1(3) . . ?
C6 C5 H5 121.0 . . ?
C6 C5 C4 118.1(3) . . ?
C4 C5 H5 121.0 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C18 C19 C14 -177.8(3) . . . . ?
F1 C18 C17 C16 177.3(3) . . . . ?
F2 C16 C17 C18 -177.1(3) . . . . ?
F2 C16 C15 C14 177.5(3) . . . . ?
O1 C10 C9 C7 -163.7(3) . . . . ?
N3 C20 C27 C32 37.4(4) . . . . ?
N3 C20 C27 C28 -142.8(3) . . . . ?
N3 C20 C21 C22 69.9(4) . . . . ?
N3 C20 C21 C26 -109.1(4) . . . . ?
N3 C13 C7 C1 175.0(2) . . . . ?
N3 C13 C7 C9 -56.3(3) . . . . ?
N3 C13 C7 C8 58.2(3) . . . . ?
N1 C10 C9 C7 17.3(3) . . . . ?
N1 C8 C7 C1 130.0(3) . . . . ?
N1 C8 C7 C9 10.5(3) . . . . ?
N1 C8 C7 C13 -106.7(3) . . . . ?
N2 C8 C7 C1 8.5(3) . . . . ?
N2 C8 C7 C9 -111.0(3) . . . . ?
N2 C8 C7 C13 131.8(2) . . . . ?
N2 C6 C5 C4 -174.7(3) . . . . ?
C20 N3 C13 C14 -100.8(3) . . . . ?
C20 N3 C13 C7 133.4(3) . . . . ?
C20 C27 C32 C31 178.7(3) . . . . ?
C20 C27 C28 C29 179.3(3) . . . . ?
C20 C21 C22 C23 -176.8(3) . . . . ?
C20 C21 C26 C25 176.3(3) . . . . ?
C27 C20 C21 C22 -110.7(3) . . . . ?
C27 C20 C21 C26 70.4(4) . . . . ?
C27 C32 C31 C30 2.4(5) . . . . ?
C27 C28 C29 C30 1.7(5) . . . . ?
C10 N1 C8 N2 116.0(3) . . . . ?
C10 N1 C8 C7 0.1(4) . . . . ?
C10 C9 C7 C1 -127.8(3) . . . . ?
C10 C9 C7 C8 -16.4(3) . . . . ?
C10 C9 C7 C13 103.7(3) . . . . ?
C32 C27 C28 C29 -1.0(5) . . . . ?
C32 C31 C30 C29 -1.7(5) . . . . ?
C2 C1 C7 C9 -69.1(4) . . . . ?
C2 C1 C7 C8 178.9(3) . . . . ?
C2 C1 C7 C13 56.5(4) . . . . ?
C2 C1 C6 N2 174.9(3) . . . . ?
C2 C1 C6 C5 -3.3(5) . . . . ?
C28 C27 C32 C31 -1.0(4) . . . . ?
C28 C29 C30 C31 -0.3(5) . . . . ?
C14 C13 C7 C1 52.3(3) . . . . ?
C14 C13 C7 C9 -179.0(3) . . . . ?
C14 C13 C7 C8 -64.5(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C1 C6 C5 C4 3.1(5) . . . . ?
C19 C18 C17 C16 -0.7(5) . . . . ?
C19 C14 C13 N3 -28.3(4) . . . . ?
C19 C14 C13 C7 92.8(4) . . . . ?
C19 C14 C15 C16 -0.2(5) . . . . ?
C17 C18 C19 C14 0.2(5) . . . . ?
C17 C16 C15 C14 -0.3(5) . . . . ?
C8 N1 C10 O1 169.9(3) . . . . ?
C8 N1 C10 C9 -11.1(4) . . . . ?
C8 N2 C6 C1 8.6(4) . . . . ?
C8 N2 C6 C5 -173.4(3) . . . . ?
C21 C20 C27 C32 -142.1(3) . . . . ?
C21 C20 C27 C28 37.7(4) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C21 C26 C25 C24 0.9(5) . . . . ?
C22 C21 C26 C25 -2.6(5) . . . . ?
C13 N3 C20 C27 -176.6(2) . . . . ?
C13 N3 C20 C21 2.9(4) . . . . ?
C13 C14 C19 C18 176.4(3) . . . . ?
C13 C14 C15 C16 -176.5(3) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C15 C14 C19 C18 0.2(5) . . . . ?
C15 C14 C13 N3 148.0(3) . . . . ?
C15 C14 C13 C7 -90.9(3) . . . . ?
C7 C1 C6 N2 -2.7(4) . . . . ?
C7 C1 C6 C5 179.1(3) . . . . ?
C26 C21 C22 C23 2.1(5) . . . . ?
C25 C24 C23 C22 -1.9(5) . . . . ?
C6 N2 C8 N1 -126.0(3) . . . . ?
C6 N2 C8 C7 -10.5(3) . . . . ?
C6 C1 C7 C9 108.2(3) . . . . ?
C6 C1 C7 C8 -3.7(3) . . . . ?
C6 C1 C7 C13 -126.2(3) . . . . ?
C6 C5 C4 C3 -1.1(5) . . . . ?
C5 C4 C3 C2 -0.8(5) . . . . ?
C11 N1 C10 O1 -1.3(5) . . . . ?
C11 N1 C10 C9 177.7(3) . . . . ?
C11 N1 C8 N2 -72.6(4) . . . . ?
C11 N1 C8 C7 171.4(3) . . . . ?
C23 C24 C25 C26 1.3(5) . . . . ?
C3 C2 C1 C7 178.4(3) . . . . ?
C3 C2 C1 C6 1.3(5) . . . . ?
C12 N2 C8 N1 94.0(3) . . . . ?
C12 N2 C8 C7 -150.6(3) . . . . ?
C12 N2 C6 C1 147.7(3) . . . . ?
C12 N2 C6 C5 -34.3(5) . . . . ?

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2293493'
loop_
_audit_author_name
_audit_author_address
JiangYonggang
;yunnandaxue
China
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2023-09-05
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C33 H31 F2 N3 O2'
_chemical_formula_moiety         'C32 H27 F2 N3 O, C H4 O'
_chemical_formula_weight         539.61
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C18(H18), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_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                   10.1447(5)
_cell_length_b                   26.4984(13)
_cell_length_c                   10.7233(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.691(2)
_cell_angle_gamma                90
_cell_volume                     2761.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    8306
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.24
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.9541.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            33519
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_theta_min         2.126
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_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             6890
_reflns_number_gt                5219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0370P)²+1.4058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6890
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.29415(10) 0.18724(4) 0.23438(12) 0.0403(3) Uani 1 1 d . . . . .
F2 F 0.74802(9) 0.22382(4) 0.47176(9) 0.0299(2) Uani 1 1 d . . . . .
O1 O 0.41856(12) 0.50022(4) 0.61703(11) 0.0244(2) Uani 1 1 d . . . . .
N1 N 0.40393(14) 0.33399(5) 0.64952(12) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.49134(13) 0.41862(5) 0.64732(11) 0.0185(3) Uani 1 1 d . . . . .
N3 N 0.32333(13) 0.37763(5) 0.21338(11) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.57373(16) 0.34939(6) 0.09433(14) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.526948 0.318088 0.089945 0.025 Uiso 1 1 calc R U . . .
C2 C 0.70822(17) 0.35043(7) 0.08608(15) 0.0263(4) Uani 1 1 d . . . . .
H2 H 0.752758 0.319911 0.075132 0.032 Uiso 1 1 calc R U . . .
C3 C 0.77689(16) 0.39592(7) 0.09386(15) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.868844 0.396582 0.088804 0.034 Uiso 1 1 calc R U . . .
C4 C 0.71195(17) 0.44057(7) 0.10900(15) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.759727 0.471733 0.115256 0.032 Uiso 1 1 calc R U . . .
C5 C 0.57715(16) 0.43975(6) 0.11501(14) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.532146 0.470478 0.123276 0.025 Uiso 1 1 calc R U . . .
C6 C 0.50757(15) 0.39418(6) 0.10899(13) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.36175(15) 0.39285(5) 0.11599(13) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.25145(15) 0.41072(5) -0.00034(13) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.26528(16) 0.40703(6) -0.12582(14) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.348373 0.394424 -0.137996 0.024 Uiso 1 1 calc R U . . .
C10 C 0.15828(16) 0.42168(6) -0.23326(15) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.167914 0.418379 -0.318428 0.027 Uiso 1 1 calc R U . . .
C11 C 0.03769(16) 0.44107(6) -0.21624(15) 0.0227(3) Uani 1 1 d . . . . .
H11 H -0.035115 0.451252 -0.289537 0.027 Uiso 1 1 calc R U . . .
C12 C 0.02375(16) 0.44556(6) -0.09158(15) 0.0218(3) Uani 1 1 d . . . . .
H12 H -0.058595 0.459006 -0.079636 0.026 Uiso 1 1 calc R U . . .
C13 C 0.12982(15) 0.43046(6) 0.01571(14) 0.0201(3) Uani 1 1 d . . . . .
H13 H 0.119469 0.433594 0.100653 0.024 Uiso 1 1 calc R U . . .
C14 C 0.42641(15) 0.36335(6) 0.33527(13) 0.0165(3) Uani 1 1 d . . . . .
H14 H 0.513096 0.382612 0.342665 0.020 Uiso 1 1 calc R U . . .
C15 C 0.45814(15) 0.30732(6) 0.34043(13) 0.0165(3) Uani 1 1 d . . . . .
C16 C 0.59127(15) 0.29076(6) 0.40415(14) 0.0188(3) Uani 1 1 d . . . . .
H16 H 0.662262 0.314281 0.441620 0.023 Uiso 1 1 calc R U . . .
C17 C 0.61763(15) 0.23964(6) 0.41161(14) 0.0214(3) Uani 1 1 d . . . . .
C18 C 0.52039(16) 0.20344(6) 0.35808(16) 0.0240(3) Uani 1 1 d . . . . .
H18 H 0.540730 0.168379 0.365286 0.029 Uiso 1 1 calc R U . . .
C19 C 0.39158(16) 0.22157(6) 0.29338(16) 0.0249(3) Uani 1 1 d . . . . .
C20 C 0.35674(16) 0.27190(6) 0.28386(15) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.265668 0.282315 0.239761 0.025 Uiso 1 1 calc R U . . .
C21 C 0.36617(14) 0.38008(6) 0.44720(13) 0.0155(3) Uani 1 1 d . . . . .
C22 C 0.34037(16) 0.43740(6) 0.44434(14) 0.0190(3) Uani 1 1 d . . . . .
H22A H 0.374637 0.453733 0.376645 0.023 Uiso 1 1 calc R U . . .
H22B H 0.240852 0.444620 0.425862 0.023 Uiso 1 1 calc R U . . .
C23 C 0.41824(15) 0.45629(6) 0.57777(14) 0.0186(3) Uani 1 1 d . . . . .
C24 C 0.47091(15) 0.36968(5) 0.58369(13) 0.0166(3) Uani 1 1 d . . . . .
H24 H 0.559418 0.355776 0.574840 0.020 Uiso 1 1 calc R U . . .
C25 C 0.27236(16) 0.32335(6) 0.57104(14) 0.0186(3) Uani 1 1 d . . . . .
C26 C 0.24138(15) 0.35016(5) 0.45404(13) 0.0161(3) Uani 1 1 d . . . . .
C27 C 0.11138(15) 0.34764(6) 0.36698(14) 0.0192(3) Uani 1 1 d . . . . .
H27 H 0.089591 0.366539 0.288416 0.023 Uiso 1 1 calc R U . . .
C28 C 0.01243(16) 0.31686(6) 0.39623(16) 0.0232(3) Uani 1 1 d . . . . .
H28 H -0.077352 0.314685 0.337185 0.028 Uiso 1 1 calc R U . . .
C29 C 0.04499(17) 0.28948(6) 0.51130(16) 0.0250(3) Uani 1 1 d . . . . .
H29 H -0.023076 0.268567 0.529855 0.030 Uiso 1 1 calc R U . . .
C30 C 0.17487(17) 0.29202(6) 0.59983(15) 0.0237(3) Uani 1 1 d . . . . .
H30 H 0.196733 0.272891 0.678034 0.028 Uiso 1 1 calc R U . . .
C31 C 0.48183(18) 0.29672(7) 0.73921(16) 0.0302(4) Uani 1 1 d . . . . .
H31A H 0.496353 0.266936 0.690600 0.045 Uiso 1 1 calc R U . . .
H31B H 0.430892 0.286979 0.800486 0.045 Uiso 1 1 calc R U . . .
H31C H 0.571077 0.310967 0.787380 0.045 Uiso 1 1 calc R U . . .
C32 C 0.59463(16) 0.42548(6) 0.77169(14) 0.0233(3) Uani 1 1 d . . . . .
H32A H 0.568358 0.406228 0.838871 0.035 Uiso 1 1 calc R U . . .
H32B H 0.601408 0.461360 0.794792 0.035 Uiso 1 1 calc R U . . .
H32C H 0.683860 0.413468 0.765387 0.035 Uiso 1 1 calc R U . . .
O2 O 0.73935(13) 0.42762(5) 0.53361(12) 0.0334(3) Uani 1 1 d . . . . .
H2A H 0.686698 0.449621 0.489227 0.050 Uiso 1 1 calc R U . . .
C33 C 0.8323(2) 0.41209(9) 0.46829(19) 0.0415(5) Uani 1 1 d . . . . .
H33A H 0.782176 0.397109 0.384550 0.062 Uiso 1 1 calc R U . . .
H33B H 0.895066 0.386985 0.520966 0.062 Uiso 1 1 calc R U . . .
H33C H 0.885287 0.441225 0.453277 0.062 Uiso 1 1 calc R U . . .


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 C19 1.3584(18) . ?
F2 C17 1.3607(17) . ?
O1 C23 1.2373(18) . ?
N1 C24 1.4594(19) . ?
N1 C25 1.387(2) . ?
N1 C31 1.445(2) . ?
N2 C23 1.3360(19) . ?
N2 C24 1.4524(19) . ?
N2 C32 1.4515(18) . ?
N3 C7 1.2802(18) . ?
N3 C14 1.4696(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(2) . ?
C1 C6 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 C7 1.503(2) . ?
C7 C8 1.494(2) . ?
C8 C9 1.396(2) . ?
C8 C13 1.396(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C14 H14 1.0000 . ?
C14 C15 1.517(2) . ?
C14 C21 1.5595(19) . ?
C15 C16 1.398(2) . ?
C15 C20 1.396(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(2) . ?
C17 C18 1.378(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(2) . ?
C19 C20 1.376(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.540(2) . ?
C21 C24 1.5665(19) . ?
C21 C26 1.513(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.507(2) . ?
C24 H24 1.0000 . ?
C25 C26 1.397(2) . ?
C25 C30 1.392(2) . ?
C26 C27 1.381(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.397(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(2) . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O2 H2A 0.8400 . ?
O2 C33 1.389(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C25 N1 C24 109.81(12) . . ?
C25 N1 C31 120.79(13) . . ?
C31 N1 C24 121.55(13) . . ?
C23 N2 C24 115.06(12) . . ?
C23 N2 C32 123.91(13) . . ?
C32 N2 C24 120.75(12) . . ?
C7 N3 C14 120.07(12) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.15(15) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.95(16) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.20(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.99(16) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.35(15) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 119.88(13) . . ?
C5 C6 C1 119.34(14) . . ?
C5 C6 C7 120.77(14) . . ?
N3 C7 C6 125.64(13) . . ?
N3 C7 C8 116.78(13) . . ?
C8 C7 C6 117.58(12) . . ?
C9 C8 C7 121.63(13) . . ?
C13 C8 C7 119.52(12) . . ?
C13 C8 C9 118.84(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.53(14) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.14(14) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.73(14) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.23(14) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.51(14) . . ?
C12 C13 H13 119.7 . . ?
N3 C14 H14 108.9 . . ?
N3 C14 C15 111.95(12) . . ?
N3 C14 C21 105.99(11) . . ?
C15 C14 H14 108.9 . . ?
C15 C14 C21 112.09(11) . . ?
C21 C14 H14 108.9 . . ?
C16 C15 C14 119.36(13) . . ?
C20 C15 C14 121.34(13) . . ?
C20 C15 C16 119.29(14) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.75(14) . . ?
C17 C16 H16 120.6 . . ?
F2 C17 C16 118.44(14) . . ?
F2 C17 C18 117.72(14) . . ?
C18 C17 C16 123.81(14) . . ?
C17 C18 H18 122.3 . . ?
C17 C18 C19 115.40(15) . . ?
C19 C18 H18 122.3 . . ?
F1 C19 C18 117.32(15) . . ?
F1 C19 C20 118.51(14) . . ?
C20 C19 C18 124.16(15) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 C15 118.55(14) . . ?
C19 C20 H20 120.7 . . ?
C14 C21 C24 111.01(11) . . ?
C22 C21 C14 111.52(11) . . ?
C22 C21 C24 104.94(11) . . ?
C26 C21 C14 114.00(12) . . ?
C26 C21 C22 112.20(12) . . ?
C26 C21 C24 102.41(11) . . ?
C21 C22 H22A 110.6 . . ?
C21 C22 H22B 110.6 . . ?
H22A C22 H22B 108.8 . . ?
C23 C22 C21 105.60(12) . . ?
C23 C22 H22A 110.6 . . ?
C23 C22 H22B 110.6 . . ?
O1 C23 N2 124.48(14) . . ?
O1 C23 C22 125.78(14) . . ?
N2 C23 C22 109.71(13) . . ?
N1 C24 C21 106.31(12) . . ?
N1 C24 H24 111.3 . . ?
N2 C24 N1 112.02(12) . . ?
N2 C24 C21 104.41(11) . . ?
N2 C24 H24 111.3 . . ?
C21 C24 H24 111.3 . . ?
N1 C25 C26 111.75(13) . . ?
N1 C25 C30 127.43(14) . . ?
C30 C25 C26 120.78(14) . . ?
C25 C26 C21 109.54(12) . . ?
C27 C26 C21 129.96(13) . . ?
C27 C26 C25 120.48(13) . . ?
C26 C27 H27 120.5 . . ?
C26 C27 C28 118.99(14) . . ?
C28 C27 H27 120.5 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.14(15) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.35(15) . . ?
C30 C29 H29 119.3 . . ?
C25 C30 H30 120.9 . . ?
C29 C30 C25 118.22(14) . . ?
C29 C30 H30 120.9 . . ?
N1 C31 H31A 109.5 . . ?
N1 C31 H31B 109.5 . . ?
N1 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N2 C32 H32A 109.5 . . ?
N2 C32 H32B 109.5 . . ?
N2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C33 O2 H2A 109.5 . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A O1 0.84 1.87 2.7103(17) 174.9 3_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C19 C20 C15 -177.71(14) . . . . ?
F2 C17 C18 C19 -177.25(13) . . . . ?
N1 C25 C26 C21 3.49(17) . . . . ?
N1 C25 C26 C27 -175.06(13) . . . . ?
N1 C25 C30 C29 175.17(15) . . . . ?
N3 C7 C8 C9 -151.26(14) . . . . ?
N3 C7 C8 C13 27.1(2) . . . . ?
N3 C14 C15 C16 146.38(13) . . . . ?
N3 C14 C15 C20 -34.22(18) . . . . ?
N3 C14 C21 C22 -60.08(15) . . . . ?
N3 C14 C21 C24 -176.72(11) . . . . ?
N3 C14 C21 C26 68.24(15) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C6 C7 N3 73.7(2) . . . . ?
C1 C6 C7 C8 -106.19(16) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 179.17(13) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C4 C5 C6 C7 179.74(13) . . . . ?
C5 C6 C7 N3 -107.24(18) . . . . ?
C5 C6 C7 C8 72.83(17) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C7 C8 C9 28.7(2) . . . . ?
C6 C7 C8 C13 -152.96(14) . . . . ?
C7 N3 C14 C15 -92.84(16) . . . . ?
C7 N3 C14 C21 144.67(13) . . . . ?
C7 C8 C9 C10 176.86(14) . . . . ?
C7 C8 C13 C12 -177.59(14) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C9 C8 C13 C12 0.8(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C13 C8 C9 C10 -1.5(2) . . . . ?
C14 N3 C7 C6 5.0(2) . . . . ?
C14 N3 C7 C8 -175.04(12) . . . . ?
C14 C15 C16 C17 178.01(13) . . . . ?
C14 C15 C20 C19 -179.14(14) . . . . ?
C14 C21 C22 C23 -124.84(12) . . . . ?
C14 C21 C24 N1 -118.48(13) . . . . ?
C14 C21 C24 N2 122.93(12) . . . . ?
C14 C21 C26 C25 115.74(13) . . . . ?
C14 C21 C26 C27 -65.9(2) . . . . ?
C15 C14 C21 C22 177.52(12) . . . . ?
C15 C14 C21 C24 60.88(15) . . . . ?
C15 C14 C21 C26 -54.15(16) . . . . ?
C15 C16 C17 F2 178.85(12) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C16 C15 C20 C19 0.3(2) . . . . ?
C16 C17 C18 C19 0.7(2) . . . . ?
C17 C18 C19 F1 177.28(14) . . . . ?
C17 C18 C19 C20 -1.9(2) . . . . ?
C18 C19 C20 C15 1.5(2) . . . . ?
C20 C15 C16 C17 -1.4(2) . . . . ?
C21 C14 C15 C16 -94.68(15) . . . . ?
C21 C14 C15 C20 84.72(16) . . . . ?
C21 C22 C23 O1 -176.44(14) . . . . ?
C21 C22 C23 N2 5.49(16) . . . . ?
C21 C26 C27 C28 -179.82(14) . . . . ?
C22 C21 C24 N1 120.90(13) . . . . ?
C22 C21 C24 N2 2.31(14) . . . . ?
C22 C21 C26 C25 -116.28(13) . . . . ?
C22 C21 C26 C27 62.09(19) . . . . ?
C23 N2 C24 N1 -113.47(14) . . . . ?
C23 N2 C24 C21 1.15(16) . . . . ?
C24 N1 C25 C26 -1.00(18) . . . . ?
C24 N1 C25 C30 -178.49(15) . . . . ?
C24 N2 C23 O1 177.62(14) . . . . ?
C24 N2 C23 C22 -4.28(17) . . . . ?
C24 C21 C22 C23 -4.56(15) . . . . ?
C24 C21 C26 C25 -4.25(15) . . . . ?
C24 C21 C26 C27 174.11(14) . . . . ?
C25 N1 C24 N2 111.68(14) . . . . ?
C25 N1 C24 C21 -1.78(16) . . . . ?
C25 C26 C27 C28 -1.6(2) . . . . ?
C26 C21 C22 C23 105.88(13) . . . . ?
C26 C21 C24 N1 3.57(15) . . . . ?
C26 C21 C24 N2 -115.02(12) . . . . ?
C26 C25 C30 C29 -2.1(2) . . . . ?
C26 C27 C28 C29 0.2(2) . . . . ?
C27 C28 C29 C30 0.3(2) . . . . ?
C28 C29 C30 C25 0.7(2) . . . . ?
C30 C25 C26 C21 -178.83(14) . . . . ?
C30 C25 C26 C27 2.6(2) . . . . ?
C31 N1 C24 N2 -99.06(17) . . . . ?
C31 N1 C24 C21 147.48(14) . . . . ?
C31 N1 C25 C26 -150.53(14) . . . . ?
C31 N1 C25 C30 32.0(2) . . . . ?
C32 N2 C23 O1 -8.4(2) . . . . ?
C32 N2 C23 C22 169.69(13) . . . . ?
C32 N2 C24 N1 72.35(17) . . . . ?
C32 N2 C24 C21 -173.02(12) . . . . ?

