# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mzl_e_501_0m
_database_code_depnum_ccdc_archive 'CCDC 2074887'
loop_
_audit_author_name
_audit_author_address
'Marchivie M.'
;university of Bordeaux
France
;
_audit_update_record             
;
2021-04-01 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
mathieu.marchivie@u-bordeaux.fr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F3 N3'
_chemical_formula_sum            'C22 H18 F3 N3'
_chemical_formula_weight         381.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.3849(12)
_cell_length_b                   5.8934(4)
_cell_length_c                   22.187(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.051(4)
_cell_angle_gamma                90
_cell_volume                     1889.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7784
_cell_measurement_temperature    299.59
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8031.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16348
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_min         1.409
_diffrn_ambient_temperature      299.59
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                4557
_reflns_number_total             6319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6319
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0820P)²+0.3594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1503
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F3AA)=1-FVAR(1)
 Sof(F3BA)=FVAR(1)
 Sof(F3BB)=1-FVAR(2)
 Sof(F3AB)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C3A(H3A), C3B(H3B)
3.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C1B(H1BA,
 H1BB), C2B(H2BA,H2BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB)
3.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A),
 C20A(H20A), C21A(H21A), C22A(H22A), C11B(H11B), C12B(H12B), C14B(H14B),
 C15B(H15B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B), C22B(H22B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 1.3543(4) 1.8243(8) 0.5029(3) 0.0621(14) Uani 1 1 d . . . . .
H1AA H 1.321027 1.901271 0.462954 0.074 Uiso 1 1 calc R U . . .
H1AB H 1.407858 1.915858 0.525772 0.074 Uiso 1 1 calc R U . . .
C2A C 1.2915(4) 1.8053(9) 0.5433(3) 0.0675(15) Uani 1 1 d . . . . .
H2AA H 1.318876 1.885330 0.583574 0.081 Uiso 1 1 calc R U . . .
H2AB H 1.231678 1.872849 0.520543 0.081 Uiso 1 1 calc R U . . .
C3A C 1.2796(3) 1.5540(8) 0.5561(2) 0.0501(12) Uani 1 1 d . . . . .
H3A H 1.237360 1.531257 0.580045 0.060 Uiso 1 1 calc R U . . .
C4A C 1.3762(4) 1.4589(9) 0.5918(2) 0.0582(14) Uani 1 1 d . . . . .
H4AA H 1.403356 1.537396 0.632325 0.070 Uiso 1 1 calc R U . . .
H4AB H 1.371862 1.298939 0.600595 0.070 Uiso 1 1 calc R U . . .
C5A C 1.4368(4) 1.4908(8) 0.5507(2) 0.0555(13) Uani 1 1 d . . . . .
H5AA H 1.489984 1.582840 0.573905 0.067 Uiso 1 1 calc R U . . .
H5AB H 1.459250 1.343990 0.542692 0.067 Uiso 1 1 calc R U . . .
C6A C 1.3056(3) 1.4658(7) 0.4581(2) 0.0371(10) Uani 1 1 d . . . . .
C7A C 1.2472(3) 1.4353(7) 0.4929(2) 0.0419(11) Uani 1 1 d . . . . .
C8A C 1.1572(3) 1.1970(8) 0.4173(2) 0.0439(11) Uani 1 1 d . . . . .
C9A C 1.2833(3) 1.3567(7) 0.3990(2) 0.0373(10) Uani 1 1 d . . . . .
C10A C 1.0807(3) 1.0284(9) 0.3964(2) 0.0485(12) Uani 1 1 d . . . . .
C11A C 1.0227(4) 0.9948(11) 0.4308(3) 0.0627(15) Uani 1 1 d . . . . .
H11A H 1.030223 1.080700 0.467386 0.075 Uiso 1 1 calc R U . . .
C12A C 0.9536(4) 0.8352(11) 0.4114(3) 0.0645(15) Uani 1 1 d . . . . .
H12A H 0.915325 0.813210 0.435507 0.077 Uiso 1 1 calc R U . . .
C13A C 0.9401(4) 0.7090(11) 0.3578(3) 0.0648(15) Uani 1 1 d . . . . .
C14A C 0.9983(5) 0.7396(14) 0.3237(3) 0.099(3) Uani 1 1 d . . . . .
H14A H 0.990623 0.652472 0.287284 0.118 Uiso 1 1 calc R U . . .
C15A C 1.0683(4) 0.8983(13) 0.3427(3) 0.085(2) Uani 1 1 d . . . . .
H15A H 1.107310 0.917384 0.319052 0.102 Uiso 1 1 calc R U . . .
C16A C 0.8644(5) 0.5372(16) 0.3334(5) 0.098(3) Uani 1 1 d . . . . .
C17A C 1.3385(3) 1.3650(7) 0.35569(19) 0.0375(10) Uani 1 1 d . . . . .
C18A C 1.3357(3) 1.1819(9) 0.3156(2) 0.0505(12) Uani 1 1 d . . . . .
H18A H 1.298591 1.057408 0.315647 0.061 Uiso 1 1 calc R U . . .
C19A C 1.3873(4) 1.1828(9) 0.2758(3) 0.0571(13) Uani 1 1 d . . . . .
H19A H 1.385142 1.059167 0.249306 0.068 Uiso 1 1 calc R U . . .
C20A C 1.4419(4) 1.3658(10) 0.2752(2) 0.0605(14) Uani 1 1 d . . . . .
H20A H 1.477868 1.364702 0.248993 0.073 Uiso 1 1 calc R U . . .
C21A C 1.4436(4) 1.5495(10) 0.3130(2) 0.0615(14) Uani 1 1 d . . . . .
H21A H 1.479287 1.675326 0.311391 0.074 Uiso 1 1 calc R U . . .
C22A C 1.3929(3) 1.5501(9) 0.3535(2) 0.0519(12) Uani 1 1 d . . . . .
H22A H 1.395241 1.675189 0.379586 0.062 Uiso 1 1 calc R U . . .
F1A F 0.7858(3) 0.6191(11) 0.3370(4) 0.183(3) Uani 1 1 d . . . A 1
F2A F 0.8670(4) 0.3920(11) 0.3803(4) 0.187(3) Uani 1 1 d . . . B 1
F3AA F 0.8837(7) 0.3560(17) 0.3060(6) 0.097(5) Uani 0.475(16) 1 d . . P A 2
F3BA F 0.8199(8) 0.548(3) 0.2714(4) 0.129(7) Uani 0.525(16) 1 d . . P A 1
N1A N 1.3858(3) 1.6015(6) 0.48826(19) 0.0454(10) Uani 1 1 d . . . . .
N2A N 1.1723(3) 1.3019(7) 0.47386(18) 0.0464(9) Uani 1 1 d . . . . .
N3A N 1.2088(3) 1.2200(6) 0.38004(18) 0.0440(9) Uani 1 1 d . . . . .
C1B C 0.3872(4) 0.1989(9) -0.0511(2) 0.0593(14) Uani 1 1 d . . . . .
H1BA H 0.413333 0.047374 -0.045006 0.071 Uiso 1 1 calc R U . . .
H1BB H 0.418968 0.287119 -0.074110 0.071 Uiso 1 1 calc R U . . .
C2B C 0.2841(4) 0.1847(10) -0.0917(2) 0.0621(14) Uani 1 1 d . . . . .
H2BA H 0.272023 0.268572 -0.131299 0.074 Uiso 1 1 calc R U . . .
H2BB H 0.266460 0.027722 -0.102304 0.074 Uiso 1 1 calc R U . . .
C3B C 0.2276(4) 0.2853(9) -0.0530(2) 0.0549(13) Uani 1 1 d . . . . .
H3B H 0.160859 0.273266 -0.075911 0.066 Uiso 1 1 calc R U . . .
C4B C 0.2591(4) 0.5335(9) -0.0380(3) 0.0688(16) Uani 1 1 d . . . . .
H4BA H 0.247313 0.617519 -0.077639 0.083 Uiso 1 1 calc R U . . .
H4BB H 0.224912 0.604823 -0.013665 0.083 Uiso 1 1 calc R U . . .
C5B C 0.3627(4) 0.5353(9) 0.0008(3) 0.0643(15) Uani 1 1 d . . . . .
H5BA H 0.394704 0.623545 -0.022011 0.077 Uiso 1 1 calc R U . . .
H5BB H 0.372392 0.608820 0.041726 0.077 Uiso 1 1 calc R U . . .
C6B C 0.3505(3) 0.1758(7) 0.0433(2) 0.0394(10) Uani 1 1 d . . . . .
C7B C 0.2573(3) 0.1613(7) 0.0097(2) 0.0430(11) Uani 1 1 d . . . . .
C8B C 0.2386(3) -0.0749(8) 0.0846(2) 0.0439(11) Uani 1 1 d . . . . .
C9B C 0.3863(3) 0.0625(7) 0.1015(2) 0.0377(10) Uani 1 1 d . . . . .
C10B C 0.1791(3) -0.2311(9) 0.1061(2) 0.0481(12) Uani 1 1 d . . . . .
C11B C 0.0889(3) -0.2648(10) 0.0696(2) 0.0610(15) Uani 1 1 d . . . . .
H11B H 0.063390 -0.183550 0.031695 0.073 Uiso 1 1 calc R U . . .
C12B C 0.0344(4) -0.4178(11) 0.0879(3) 0.0649(15) Uani 1 1 d . . . . .
H12B H -0.027043 -0.438677 0.062058 0.078 Uiso 1 1 calc R U . . .
C13B C 0.0695(4) -0.5373(10) 0.1429(3) 0.0629(15) Uani 1 1 d . . . . .
C14B C 0.1596(4) -0.5007(14) 0.1811(4) 0.104(3) Uani 1 1 d . . . . .
H14B H 0.184261 -0.578164 0.219752 0.125 Uiso 1 1 calc R U . . .
C15B C 0.2143(4) -0.3485(14) 0.1623(3) 0.095(2) Uani 1 1 d . . . . .
H15B H 0.275551 -0.326315 0.188253 0.114 Uiso 1 1 calc R U . . .
C16B C 0.0129(5) -0.7030(15) 0.1632(4) 0.089(2) Uani 1 1 d . . . . .
C17B C 0.4833(3) 0.0612(8) 0.1444(2) 0.0397(10) Uani 1 1 d . . . . .
C18B C 0.5165(3) -0.1211(9) 0.1856(2) 0.0477(12) Uani 1 1 d . . . . .
H18B H 0.477246 -0.241757 0.185046 0.057 Uiso 1 1 calc R U . . .
C19B C 0.6060(3) -0.1262(10) 0.2271(3) 0.0597(14) Uani 1 1 d . . . . .
H19B H 0.626947 -0.250131 0.254094 0.072 Uiso 1 1 calc R U . . .
C20B C 0.6651(4) 0.0508(12) 0.2290(3) 0.0669(15) Uani 1 1 d . . . . .
H20B H 0.725855 0.046914 0.257215 0.080 Uiso 1 1 calc R U . . .
C21B C 0.6340(4) 0.2329(10) 0.1890(3) 0.0631(15) Uani 1 1 d . . . . .
H21B H 0.673790 0.352954 0.190104 0.076 Uiso 1 1 calc R U . . .
C22B C 0.5436(4) 0.2390(8) 0.1469(2) 0.0514(13) Uani 1 1 d . . . . .
H22B H 0.523095 0.363564 0.120032 0.062 Uiso 1 1 calc R U . . .
F1B F -0.0344(5) -0.8363(11) 0.1162(3) 0.174(3) Uani 1 1 d . . . C 1
F2B F -0.0600(5) -0.6076(12) 0.1710(4) 0.184(3) Uani 1 1 d . . . C 1
F3AB F 0.0330(10) -0.726(4) 0.2252(6) 0.120(9) Uani 0.47(2) 1 d . . P C 1
F3BB F 0.0571(6) -0.887(2) 0.1915(9) 0.114(7) Uani 0.53(2) 1 d . . P C 2
N1B N 0.4029(3) 0.3043(6) 0.01242(19) 0.0486(10) Uani 1 1 d . . . . .
N2B N 0.1988(3) 0.0376(7) 0.02913(19) 0.0483(10) Uani 1 1 d . . . . .
N3B N 0.3276(3) -0.0655(6) 0.12104(17) 0.0436(9) 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
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A C2A 1.532(8) . ?
C1A N1A 1.473(6) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.531(8) . ?
C3A H3A 0.9800 . ?
C3A C4A 1.530(7) . ?
C3A C7A 1.492(6) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.523(7) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A N1A 1.488(6) . ?
C6A C7A 1.382(6) . ?
C6A C9A 1.393(6) . ?
C6A N1A 1.430(5) . ?
C7A N2A 1.338(6) . ?
C8A C10A 1.487(6) . ?
C8A N2A 1.345(6) . ?
C8A N3A 1.336(6) . ?
C9A C17A 1.485(6) . ?
C9A N3A 1.345(5) . ?
C10A C11A 1.373(6) . ?
C10A C15A 1.373(8) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.374(8) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.357(8) . ?
C13A C14A 1.369(8) . ?
C13A C16A 1.497(9) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.378(8) . ?
C15A H15A 0.9300 . ?
C16A F1A 1.330(10) . ?
C16A F2A 1.336(10) . ?
C16A F3AA 1.312(12) . ?
C16A F3BA 1.311(12) . ?
C17A C18A 1.390(7) . ?
C17A C22A 1.386(6) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.374(7) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.370(7) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.364(8) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.378(7) . ?
C22A H22A 0.9300 . ?
F1A F3BA 1.759(11) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C1B C2B 1.534(8) . ?
C1B N1B 1.483(6) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.533(7) . ?
C3B H3B 0.9800 . ?
C3B C4B 1.541(8) . ?
C3B C7B 1.499(7) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.530(8) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B N1B 1.481(7) . ?
C6B C7B 1.373(6) . ?
C6B C9B 1.390(6) . ?
C6B N1B 1.439(6) . ?
C7B N2B 1.338(6) . ?
C8B C10B 1.488(6) . ?
C8B N2B 1.347(6) . ?
C8B N3B 1.332(6) . ?
C9B C17B 1.470(6) . ?
C9B N3B 1.356(5) . ?
C10B C11B 1.361(7) . ?
C10B C15B 1.364(8) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.383(7) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.352(8) . ?
C13B C14B 1.372(8) . ?
C13B C16B 1.477(9) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.387(8) . ?
C15B H15B 0.9300 . ?
C16B F1B 1.309(9) . ?
C16B F2B 1.319(10) . ?
C16B F3AB 1.309(13) . ?
C16B F3BB 1.317(12) . ?
C17B C18B 1.389(7) . ?
C17B C22B 1.388(6) . ?
C18B H18B 0.9300 . ?
C18B C19B 1.369(7) . ?
C19B H19B 0.9300 . ?
C19B C20B 1.375(8) . ?
C20B H20B 0.9300 . ?
C20B C21B 1.370(9) . ?
C21B H21B 0.9300 . ?
C21B C22B 1.384(7) . ?
C22B H22B 0.9300 . ?
F2B F3AB 1.674(17) . ?

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
H1AA C1A H1AB 107.8 . . ?
C2A C1A H1AA 109.1 . . ?
C2A C1A H1AB 109.1 . . ?
N1A C1A H1AA 109.1 . . ?
N1A C1A H1AB 109.1 . . ?
N1A C1A C2A 112.6(4) . . ?
C1A C2A H2AA 110.0 . . ?
C1A C2A H2AB 110.0 . . ?
H2AA C2A H2AB 108.4 . . ?
C3A C2A C1A 108.6(4) . . ?
C3A C2A H2AA 110.0 . . ?
C3A C2A H2AB 110.0 . . ?
C2A C3A H3A 112.1 . . ?
C4A C3A C2A 107.1(5) . . ?
C4A C3A H3A 112.1 . . ?
C7A C3A C2A 107.6(4) . . ?
C7A C3A H3A 112.1 . . ?
C7A C3A C4A 105.5(4) . . ?
C3A C4A H4AA 109.8 . . ?
C3A C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.3 . . ?
C5A C4A C3A 109.3(4) . . ?
C5A C4A H4AA 109.8 . . ?
C5A C4A H4AB 109.8 . . ?
C4A C5A H5AA 109.2 . . ?
C4A C5A H5AB 109.2 . . ?
H5AA C5A H5AB 107.9 . . ?
N1A C5A C4A 112.1(4) . . ?
N1A C5A H5AA 109.2 . . ?
N1A C5A H5AB 109.2 . . ?
C7A C6A C9A 117.9(4) . . ?
C7A C6A N1A 115.7(4) . . ?
C9A C6A N1A 126.4(4) . . ?
C6A C7A C3A 113.1(4) . . ?
N2A C7A C3A 123.1(4) . . ?
N2A C7A C6A 123.7(4) . . ?
N2A C8A C10A 117.6(4) . . ?
N3A C8A C10A 116.6(4) . . ?
N3A C8A N2A 125.6(4) . . ?
C6A C9A C17A 125.7(4) . . ?
N3A C9A C6A 118.7(4) . . ?
N3A C9A C17A 115.6(4) . . ?
C11A C10A C8A 121.2(4) . . ?
C15A C10A C8A 120.3(4) . . ?
C15A C10A C11A 118.5(5) . . ?
C10A C11A H11A 119.8 . . ?
C10A C11A C12A 120.4(5) . . ?
C12A C11A H11A 119.8 . . ?
C11A C12A H12A 119.4 . . ?
C13A C12A C11A 121.3(5) . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C14A 118.7(5) . . ?
C12A C13A C16A 123.6(6) . . ?
C14A C13A C16A 117.7(6) . . ?
C13A C14A H14A 119.6 . . ?
C13A C14A C15A 120.7(6) . . ?
C15A C14A H14A 119.6 . . ?
C10A C15A C14A 120.4(5) . . ?
C10A C15A H15A 119.8 . . ?
C14A C15A H15A 119.8 . . ?
F1A C16A C13A 110.1(8) . . ?
F1A C16A F2A 88.3(6) . . ?
F2A C16A C13A 109.9(7) . . ?
F3AA C16A C13A 116.5(6) . . ?
F3BA C16A C13A 114.1(7) . . ?
F3BA C16A F1A 83.5(8) . . ?
F3BA C16A F2A 135.4(8) . . ?
C18A C17A C9A 119.4(4) . . ?
C22A C17A C9A 122.3(4) . . ?
C22A C17A C18A 118.3(4) . . ?
C17A C18A H18A 119.7 . . ?
C19A C18A C17A 120.7(5) . . ?
C19A C18A H18A 119.7 . . ?
C18A C19A H19A 120.0 . . ?
C20A C19A C18A 120.1(5) . . ?
C20A C19A H19A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 120.1(4) . . ?
C21A C20A H20A 120.0 . . ?
C20A C21A H21A 119.8 . . ?
C20A C21A C22A 120.4(5) . . ?
C22A C21A H21A 119.8 . . ?
C17A C22A H22A 119.8 . . ?
C21A C22A C17A 120.3(5) . . ?
C21A C22A H22A 119.8 . . ?
C16A F1A F3BA 47.8(6) . . ?
C16A F3BA F1A 48.7(5) . . ?
C1A N1A C5A 107.1(4) . . ?
C6A N1A C1A 107.8(4) . . ?
C6A N1A C5A 106.6(3) . . ?
C7A N2A C8A 114.7(4) . . ?
C8A N3A C9A 119.4(4) . . ?
H1BA C1B H1BB 107.9 . . ?
C2B C1B H1BA 109.1 . . ?
C2B C1B H1BB 109.1 . . ?
N1B C1B H1BA 109.1 . . ?
N1B C1B H1BB 109.1 . . ?
N1B C1B C2B 112.3(4) . . ?
C1B C2B H2BA 109.9 . . ?
C1B C2B H2BB 109.9 . . ?
H2BA C2B H2BB 108.3 . . ?
C3B C2B C1B 108.7(4) . . ?
C3B C2B H2BA 109.9 . . ?
C3B C2B H2BB 109.9 . . ?
C2B C3B H3B 112.1 . . ?
C2B C3B C4B 107.0(5) . . ?
C4B C3B H3B 112.1 . . ?
C7B C3B C2B 106.3(4) . . ?
C7B C3B H3B 112.1 . . ?
C7B C3B C4B 106.8(5) . . ?
C3B C4B H4BA 110.0 . . ?
C3B C4B H4BB 110.0 . . ?
H4BA C4B H4BB 108.4 . . ?
C5B C4B C3B 108.5(5) . . ?
C5B C4B H4BA 110.0 . . ?
C5B C4B H4BB 110.0 . . ?
C4B C5B H5BA 109.1 . . ?
C4B C5B H5BB 109.1 . . ?
H5BA C5B H5BB 107.8 . . ?
N1B C5B C4B 112.6(4) . . ?
N1B C5B H5BA 109.1 . . ?
N1B C5B H5BB 109.1 . . ?
C7B C6B C9B 118.8(4) . . ?
C7B C6B N1B 115.2(4) . . ?
C9B C6B N1B 126.0(4) . . ?
C6B C7B C3B 113.7(4) . . ?
N2B C7B C3B 122.7(4) . . ?
N2B C7B C6B 123.5(4) . . ?
N2B C8B C10B 117.5(4) . . ?
N3B C8B C10B 116.7(4) . . ?
N3B C8B N2B 125.8(4) . . ?
C6B C9B C17B 126.5(4) . . ?
N3B C9B C6B 118.0(4) . . ?
N3B C9B C17B 115.5(4) . . ?
C11B C10B C8B 120.9(4) . . ?
C11B C10B C15B 118.3(5) . . ?
C15B C10B C8B 120.8(5) . . ?
C10B C11B H11B 119.4 . . ?
C10B C11B C12B 121.2(5) . . ?
C12B C11B H11B 119.4 . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B C11B 120.6(5) . . ?
C13B C12B H12B 119.7 . . ?
C12B C13B C14B 118.8(5) . . ?
C12B C13B C16B 121.6(6) . . ?
C14B C13B C16B 119.6(6) . . ?
C13B C14B H14B 119.8 . . ?
C13B C14B C15B 120.3(6) . . ?
C15B C14B H14B 119.8 . . ?
C10B C15B C14B 120.7(6) . . ?
C10B C15B H15B 119.7 . . ?
C14B C15B H15B 119.7 . . ?
F1B C16B C13B 112.3(6) . . ?
F1B C16B F2B 95.4(7) . . ?
F1B C16B F3AB 129.8(9) . . ?
F2B C16B C13B 112.0(7) . . ?
F3AB C16B C13B 115.9(7) . . ?
F3AB C16B F2B 79.1(12) . . ?
F3BB C16B C13B 115.2(7) . . ?
C18B C17B C9B 119.5(4) . . ?
C22B C17B C9B 122.6(4) . . ?
C22B C17B C18B 117.9(4) . . ?
C17B C18B H18B 119.4 . . ?
C19B C18B C17B 121.1(5) . . ?
C19B C18B H18B 119.4 . . ?
C18B C19B H19B 119.8 . . ?
C18B C19B C20B 120.4(5) . . ?
C20B C19B H19B 119.8 . . ?
C19B C20B H20B 120.2 . . ?
C21B C20B C19B 119.6(5) . . ?
C21B C20B H20B 120.2 . . ?
C20B C21B H21B 119.9 . . ?
C20B C21B C22B 120.3(5) . . ?
C22B C21B H21B 119.9 . . ?
C17B C22B H22B 119.7 . . ?
C21B C22B C17B 120.7(5) . . ?
C21B C22B H22B 119.7 . . ?
C16B F2B F3AB 50.2(8) . . ?
C16B F3AB F2B 50.7(6) . . ?
C5B N1B C1B 107.3(4) . . ?
C6B N1B C1B 107.2(4) . . ?
C6B N1B C5B 107.3(4) . . ?
C7B N2B C8B 114.7(4) . . ?
C8B N3B C9B 119.2(4) . . ?

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
C2A H2AB N2A 0.97 2.77 3.516(7) 134.6 1_565 yes
C3A H3A F2A 0.98 2.97 3.637(8) 126.1 2_766 yes
C15A H15A F3BB 0.93 2.91 3.535(15) 126.2 1_675 yes
C19A H19A N3B 0.93 2.77 3.552(6) 141.8 1_665 yes
C3B H3B F1B 0.98 2.95 3.594(7) 124.5 2_565 yes
C4B H4BB N2B 0.97 2.80 3.586(7) 138.8 1_565 yes
C12B H12B N2B 0.93 2.73 3.646(7) 170.3 2_545 yes
C19B H19B F1A 0.93 2.62 3.351(8) 135.9 1_545 yes
C21B H21B F3BA 0.93 2.62 3.374(9) 138.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C4A 59.5(6) . . . . ?
C1A C2A C3A C7A -53.5(6) . . . . ?
C2A C1A N1A C5A -59.1(6) . . . . ?
C2A C1A N1A C6A 55.2(6) . . . . ?
C2A C3A C4A C5A -59.1(5) . . . . ?
C2A C3A C7A C6A 56.1(6) . . . . ?
C2A C3A C7A N2A -127.8(5) . . . . ?
C3A C4A C5A N1A -0.5(6) . . . . ?
C3A C7A N2A C8A -175.7(4) . . . . ?
C4A C3A C7A C6A -58.0(5) . . . . ?
C4A C3A C7A N2A 118.1(5) . . . . ?
C4A C5A N1A C1A 59.6(5) . . . . ?
C4A C5A N1A C6A -55.5(5) . . . . ?
C6A C7A N2A C8A 0.0(6) . . . . ?
C6A C9A C17A C18A 150.8(4) . . . . ?
C6A C9A C17A C22A -29.3(6) . . . . ?
C6A C9A N3A C8A 1.6(6) . . . . ?
C7A C3A C4A C5A 55.3(5) . . . . ?
C7A C6A C9A C17A -178.6(4) . . . . ?
C7A C6A C9A N3A -2.8(6) . . . . ?
C7A C6A N1A C1A -57.2(5) . . . . ?
C7A C6A N1A C5A 57.5(5) . . . . ?
C8A C10A C11A C12A -178.7(5) . . . . ?
C8A C10A C15A C14A 179.1(6) . . . . ?
C9A C6A C7A C3A 178.2(4) . . . . ?
C9A C6A C7A N2A 2.1(7) . . . . ?
C9A C6A N1A C1A 125.3(5) . . . . ?
C9A C6A N1A C5A -119.9(5) . . . . ?
C9A C17A C18A C19A -178.8(5) . . . . ?
C9A C17A C22A C21A 179.4(5) . . . . ?
C10A C8A N2A C7A 174.0(4) . . . . ?
C10A C8A N3A C9A -174.9(4) . . . . ?
C10A C11A C12A C13A -0.8(9) . . . . ?
C11A C10A C15A C14A 0.7(10) . . . . ?
C11A C12A C13A C14A 1.5(10) . . . . ?
C11A C12A C13A C16A -178.3(6) . . . . ?
C12A C13A C14A C15A -1.1(12) . . . . ?
C12A C13A C16A F1A 42.9(10) . . . . ?
C12A C13A C16A F2A -52.8(11) . . . . ?
C12A C13A C16A F3AA -145.6(9) . . . . ?
C12A C13A C16A F3BA 134.8(10) . . . . ?
C13A C14A C15A C10A 0.0(12) . . . . ?
C13A C16A F1A F3BA 113.3(8) . . . . ?
C13A C16A F3BA F1A -109.2(10) . . . . ?
C14A C13A C16A F1A -136.9(9) . . . . ?
C14A C13A C16A F2A 127.4(8) . . . . ?
C14A C13A C16A F3AA 34.7(12) . . . . ?
C14A C13A C16A F3BA -45.0(13) . . . . ?
C15A C10A C11A C12A -0.3(9) . . . . ?
C16A C13A C14A C15A 178.7(7) . . . . ?
C17A C9A N3A C8A 177.8(4) . . . . ?
C17A C18A C19A C20A -0.3(8) . . . . ?
C18A C17A C22A C21A -0.7(7) . . . . ?
C18A C19A C20A C21A -1.5(9) . . . . ?
C19A C20A C21A C22A 2.1(9) . . . . ?
C20A C21A C22A C17A -0.9(8) . . . . ?
C22A C17A C18A C19A 1.3(7) . . . . ?
F2A C16A F1A F3BA -136.1(9) . . . . ?
F2A C16A F3BA F1A 81.0(12) . . . . ?
N1A C1A C2A C3A -0.5(7) . . . . ?
N1A C6A C7A C3A 0.5(6) . . . . ?
N1A C6A C7A N2A -175.6(4) . . . . ?
N1A C6A C9A C17A -1.2(7) . . . . ?
N1A C6A C9A N3A 174.6(4) . . . . ?
N2A C8A C10A C11A 5.3(7) . . . . ?
N2A C8A C10A C15A -173.0(6) . . . . ?
N2A C8A N3A C9A 0.6(7) . . . . ?
N3A C8A C10A C11A -178.8(5) . . . . ?
N3A C8A C10A C15A 2.8(8) . . . . ?
N3A C8A N2A C7A -1.4(7) . . . . ?
N3A C9A C17A C18A -25.0(6) . . . . ?
N3A C9A C17A C22A 154.8(4) . . . . ?
C1B C2B C3B C4B 59.7(6) . . . . ?
C1B C2B C3B C7B -54.2(5) . . . . ?
C2B C1B N1B C5B -59.3(5) . . . . ?
C2B C1B N1B C6B 55.7(5) . . . . ?
C2B C3B C4B C5B -59.9(6) . . . . ?
C2B C3B C7B C6B 57.5(5) . . . . ?
C2B C3B C7B N2B -118.8(5) . . . . ?
C3B C4B C5B N1B 0.4(7) . . . . ?
C3B C7B N2B C8B 175.5(4) . . . . ?
C4B C3B C7B C6B -56.4(5) . . . . ?
C4B C3B C7B N2B 127.2(5) . . . . ?
C4B C5B N1B C1B 59.1(6) . . . . ?
C4B C5B N1B C6B -55.8(6) . . . . ?
C6B C7B N2B C8B -0.5(6) . . . . ?
C6B C9B C17B C18B -154.1(4) . . . . ?
C6B C9B C17B C22B 27.7(7) . . . . ?
C6B C9B N3B C8B -1.1(6) . . . . ?
C7B C3B C4B C5B 53.6(6) . . . . ?
C7B C6B C9B C17B -179.0(4) . . . . ?
C7B C6B C9B N3B 2.9(6) . . . . ?
C7B C6B N1B C1B -57.2(5) . . . . ?
C7B C6B N1B C5B 57.8(5) . . . . ?
C8B C10B C11B C12B 176.9(5) . . . . ?
C8B C10B C15B C14B -177.5(7) . . . . ?
C9B C6B C7B C3B -178.5(4) . . . . ?
C9B C6B C7B N2B -2.1(6) . . . . ?
C9B C6B N1B C1B 120.5(5) . . . . ?
C9B C6B N1B C5B -124.4(5) . . . . ?
C9B C17B C18B C19B -178.8(4) . . . . ?
C9B C17B C22B C21B 178.6(4) . . . . ?
C10B C8B N2B C7B -174.9(4) . . . . ?
C10B C8B N3B C9B 175.7(4) . . . . ?
C10B C11B C12B C13B 0.3(9) . . . . ?
C11B C10B C15B C14B 0.9(11) . . . . ?
C11B C12B C13B C14B 1.4(10) . . . . ?
C11B C12B C13B C16B -179.5(7) . . . . ?
C12B C13B C14B C15B -2.0(12) . . . . ?
C12B C13B C16B F1B 46.0(11) . . . . ?
C12B C13B C16B F2B -60.0(10) . . . . ?
C12B C13B C16B F3AB -148.3(15) . . . . ?
C12B C13B C16B F3BB 143.2(12) . . . . ?
C13B C14B C15B C10B 0.8(13) . . . . ?
C13B C16B F2B F3AB -113.7(10) . . . . ?
C13B C16B F3AB F2B 109.3(10) . . . . ?
C14B C13B C16B F1B -134.8(8) . . . . ?
C14B C13B C16B F2B 119.1(9) . . . . ?
C14B C13B C16B F3AB 30.8(17) . . . . ?
C14B C13B C16B F3BB -37.7(14) . . . . ?
C15B C10B C11B C12B -1.5(9) . . . . ?
C16B C13B C14B C15B 178.9(8) . . . . ?
C17B C9B N3B C8B -179.5(4) . . . . ?
C17B C18B C19B C20B 0.3(8) . . . . ?
C18B C17B C22B C21B 0.4(7) . . . . ?
C18B C19B C20B C21B -0.1(8) . . . . ?
C19B C20B C21B C22B 0.0(9) . . . . ?
C20B C21B C22B C17B -0.2(8) . . . . ?
C22B C17B C18B C19B -0.5(7) . . . . ?
F1B C16B F2B F3AB 129.5(9) . . . . ?
F1B C16B F3AB F2B -88.0(14) . . . . ?
N1B C1B C2B C3B -0.2(6) . . . . ?
N1B C6B C7B C3B -0.5(5) . . . . ?
N1B C6B C7B N2B 175.8(4) . . . . ?
N1B C6B C9B C17B 3.3(7) . . . . ?
N1B C6B C9B N3B -174.8(4) . . . . ?
N2B C8B C10B C11B 2.5(7) . . . . ?
N2B C8B C10B C15B -179.1(6) . . . . ?
N2B C8B N3B C9B -1.7(7) . . . . ?
N3B C8B C10B C11B -175.1(5) . . . . ?
N3B C8B C10B C15B 3.3(8) . . . . ?
N3B C8B N2B C7B 2.5(7) . . . . ?
N3B C9B C17B C18B 24.1(6) . . . . ?
N3B C9B C17B C22B -154.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
