# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_DS_B1_0025
_database_code_depnum_ccdc_archive 'CCDC 1914926'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/1

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Hanna Stewart'
_cambridge_user_crsid            hlo28
_cambridge_supervisor_name       'David Spring'
_cambridge_supervisor_crsid      drs36
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             HLS732
_cambridge_data_id               DS_B1_0025
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 F3 N4 +, Cl -'
_chemical_formula_sum            'C25 H22 Cl F3 N4'
_chemical_formula_weight         470.91
_chemical_absolute_configuration ad

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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 '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                   5.6933(4)
_cell_length_b                   12.7845(10)
_cell_length_c                   15.7666(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.160(7)
_cell_angle_gamma                90
_cell_volume                     1132.95(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3058
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      65.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.887
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4585
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_special_details           
;
The crystals were plates with ca 5 micron thickness. To achieve significant
diffracted intensity, a large plate was chosen, which exceded the beam
diameter in its major dimensions. This produced reasonable intensity
to 0.84 angstrom resolution (I/sigma falling below 3 around 0.9 angstrom).
Clearly, this crystal shape is not ideal, and the R(int) value is
correspondingly higher than might otherwise be hoped. For the available
crytals, however, the result is good, especially for the absolute structure,
which is the principal point of interest.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10800
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.839
_diffrn_reflns_theta_max         66.770
_diffrn_reflns_theta_full        66.770
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3903
_reflns_number_gt                2319
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.948

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The benzene ring C19-C24 is modelled as two components with complete
rings defined for both components. Atoms C19 and C22 are nominally
split, but constrained to the same site and with the same ADPs. ISOR
restraints are applied to the genuinely split atoms C20/C21/C23/C24.

The ring C6-C11 shows elongated (prolate) ADPs, which could perhaps
be split into two components. It was felt that whis would
over-complicate the model (especially because the data-to-parameter
ratio is at the lower end of expectations), so the elongated 
ellipsoids were retained.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+2.3325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_abs_structure_details 
;
Flack x determined using 654 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         3903
_refine_ls_number_parameters     335
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0854
_refine_ls_wR_factor_ref         0.2028
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.069

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
Cl1 Cl 0.2358(4) 0.6731(3) 0.4901(2) 0.0534(8) Uani 1 1 d . . . . .
F1 F 0.618(2) 0.4330(8) 0.0471(5) 0.122(4) Uani 1 1 d . . . . .
F2 F 0.929(2) 0.5219(10) 0.0656(6) 0.111(4) Uani 1 1 d . . . . .
F3 F 0.6027(19) 0.5979(8) 0.0516(5) 0.106(4) Uani 1 1 d . . . . .
N1 N 0.5235(16) 0.4843(7) 0.6928(6) 0.039(2) Uani 1 1 d . . . . .
N2 N 0.3307(16) 0.3707(8) 0.5930(6) 0.047(2) Uani 1 1 d . . . . .
N3 N 0.4964(16) 0.4283(6) 0.5593(6) 0.038(2) Uani 1 1 d . . . . .
N4 N 0.7475(14) 0.5852(5) 0.5015(5) 0.032(2) Uani 1 1 d . . . . .
H4A H 0.867060 0.625063 0.486725 0.038 Uiso 1 1 calc R U . . .
H4B H 0.608320 0.620084 0.485121 0.038 Uiso 1 1 calc R U . . .
C1 C 0.356(2) 0.4041(9) 0.6735(7) 0.043(3) Uani 1 1 d . . . . .
C2 C 0.5987(19) 0.4957(8) 0.6186(7) 0.036(2) Uani 1 1 d . . . . .
C3 C 0.7864(18) 0.5713(7) 0.5969(6) 0.030(2) Uani 1 1 d . . . . .
H3A H 0.947440 0.540101 0.615446 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7386(18) 0.4826(7) 0.4538(7) 0.031(2) Uani 1 1 d . . . . .
H4 H 0.880870 0.439838 0.477727 0.037 Uiso 1 1 calc R U . A 1
C5 C 0.514(2) 0.4252(8) 0.4691(7) 0.039(3) Uani 1 1 d . . . . .
H5A H 0.372390 0.458801 0.435446 0.046 Uiso 1 1 calc R U . . .
H5B H 0.519948 0.351656 0.449930 0.046 Uiso 1 1 calc R U . . .
C6 C 0.215(2) 0.3666(9) 0.7354(8) 0.043(3) Uani 1 1 d . . . . .
C7 C 0.015(2) 0.3091(12) 0.7085(10) 0.068(4) Uani 1 1 d . . . . .
H7A H -0.027253 0.292187 0.649385 0.081 Uiso 1 1 calc R U . . .
C8 C -0.128(2) 0.2748(18) 0.7675(11) 0.108(8) Uani 1 1 d . . . . .
H8A H -0.265506 0.233700 0.748170 0.130 Uiso 1 1 calc R U . . .
C9 C -0.072(3) 0.3003(16) 0.8535(11) 0.096(7) Uani 1 1 d . . . . .
H9A H -0.173731 0.279813 0.892916 0.115 Uiso 1 1 calc R U . . .
C10 C 0.132(3) 0.3556(13) 0.8811(9) 0.077(5) Uani 1 1 d . . . . .
H10A H 0.176343 0.371088 0.940446 0.093 Uiso 1 1 calc R U . . .
C11 C 0.275(3) 0.3892(10) 0.8223(8) 0.057(4) Uani 1 1 d . . . . .
H11A H 0.415436 0.427950 0.841908 0.068 Uiso 1 1 calc R U . . .
C12 C 0.7766(16) 0.6796(8) 0.6398(6) 0.036(2) Uani 1 1 d . . . . .
H12A H 0.871862 0.729371 0.611270 0.043 Uiso 1 1 calc R U . . .
H12B H 0.609772 0.704386 0.629527 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8642(17) 0.6827(9) 0.7339(7) 0.036(2) Uani 1 1 d . . . . .
C14 C 0.727(2) 0.7249(11) 0.7903(8) 0.061(4) Uani 1 1 d . . . . .
H14A H 0.572768 0.750480 0.768274 0.073 Uiso 1 1 calc R U . . .
C15 C 0.806(3) 0.7310(13) 0.8768(9) 0.078(5) Uani 1 1 d . . . . .
H15A H 0.707763 0.760913 0.913740 0.094 Uiso 1 1 calc R U . . .
C16 C 1.027(3) 0.6940(12) 0.9098(8) 0.070(4) Uani 1 1 d . . . . .
H16A H 1.082049 0.696977 0.969859 0.085 Uiso 1 1 calc R U . . .
C17 C 1.166(3) 0.6527(10) 0.8558(8) 0.062(4) Uani 1 1 d . . . . .
H17A H 1.319911 0.627187 0.878788 0.075 Uiso 1 1 calc R U . . .
C18 C 1.090(2) 0.6471(9) 0.7690(8) 0.054(3) Uani 1 1 d . . . . .
H18A H 1.191388 0.618821 0.732520 0.065 Uiso 1 1 calc R U . . .
C19 C 0.7350(17) 0.4972(8) 0.3592(7) 0.035(2) Uani 0.55(3) 1 d . . P B 1
C20 C 0.696(5) 0.5870(17) 0.3200(14) 0.038(6) Uani 0.55(3) 1 d . U P B 1
H20A H 0.674755 0.648076 0.352287 0.046 Uiso 0.55(3) 1 calc R U P B 1
C21 C 0.684(4) 0.5938(16) 0.2324(14) 0.038(6) Uani 0.55(3) 1 d . U P B 1
H21A H 0.649429 0.659607 0.205337 0.045 Uiso 0.55(3) 1 calc R U P B 1
C22 C 0.721(2) 0.5096(9) 0.1825(7) 0.042(3) Uani 0.55(3) 1 d . . P B 1
C23 C 0.785(5) 0.414(2) 0.2276(16) 0.048(7) Uani 0.55(3) 1 d . U P B 1
H23A H 0.823264 0.353789 0.196889 0.058 Uiso 0.55(3) 1 calc R U P B 1
C24 C 0.792(5) 0.408(2) 0.3164(15) 0.045(7) Uani 0.55(3) 1 d . U P B 1
H24A H 0.834406 0.344934 0.346787 0.054 Uiso 0.55(3) 1 calc R U P B 1
C19A C 0.7350(17) 0.4972(8) 0.3592(7) 0.035(2) Uani 0.45(3) 1 d . . P B 2
C20A C 0.550(5) 0.562(2) 0.3031(16) 0.035(7) Uani 0.45(3) 1 d . U P B 2
H20B H 0.438224 0.600967 0.329162 0.042 Uiso 0.45(3) 1 calc R U P B 2
C21A C 0.540(5) 0.567(2) 0.2160(16) 0.039(7) Uani 0.45(3) 1 d . U P B 2
H21B H 0.421536 0.606376 0.180179 0.047 Uiso 0.45(3) 1 calc R U P B 2
C22A C 0.721(2) 0.5096(9) 0.1825(7) 0.042(3) Uani 0.45(3) 1 d . . P B 2
C23A C 0.883(5) 0.453(2) 0.2267(18) 0.037(7) Uani 0.45(3) 1 d . U P B 2
H23B H 0.995493 0.417023 0.198912 0.045 Uiso 0.45(3) 1 calc R U P B 2
C24A C 0.894(5) 0.446(2) 0.3144(18) 0.034(7) Uani 0.45(3) 1 d . U P B 2
H24B H 1.015478 0.403503 0.345931 0.041 Uiso 0.45(3) 1 calc R U P B 2
C25 C 0.719(3) 0.5151(10) 0.0892(9) 0.059(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
F1 C25 1.324(15) . ?
F2 C25 1.308(16) . ?
F3 C25 1.337(15) . ?
N1 C2 1.316(13) . ?
N1 C1 1.400(14) . ?
N2 C1 1.326(14) . ?
N2 N3 1.369(11) . ?
N3 C2 1.336(13) . ?
N3 C5 1.441(12) . ?
N4 C3 1.495(12) . ?
N4 C4 1.509(11) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
C1 C6 1.443(14) . ?
C2 C3 1.520(13) . ?
C3 C12 1.546(13) . ?
C3 H3A 1.0000 . ?
C4 C19A 1.499(14) . ?
C4 C19 1.499(14) . ?
C4 C5 1.526(14) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.363(17) . ?
C6 C11 1.388(16) . ?
C7 C8 1.402(17) . ?
C7 H7A 0.9500 . ?
C8 C9 1.38(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.37(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(16) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.489(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.383(14) . ?
C13 C18 1.391(15) . ?
C14 C15 1.368(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.37(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.360(18) . ?
C16 H16A 0.9500 . ?
C17 C18 1.371(16) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.31(2) . ?
C19 C24 1.39(2) . ?
C20 C21 1.38(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.37(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.43(3) . ?
C22 C25 1.471(17) . ?
C23 C24 1.40(3) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C19A C24A 1.40(3) . ?
C19A C20A 1.51(3) . ?
C20A C21A 1.37(3) . ?
C20A H20B 0.9500 . ?
C21A C22A 1.43(3) . ?
C21A H21B 0.9500 . ?
C22A C23A 1.29(3) . ?
C22A C25 1.471(17) . ?
C23A C24A 1.38(4) . ?
C23A H23B 0.9500 . ?
C24A H24B 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
C2 N1 C1 101.2(9) . . ?
C1 N2 N3 102.8(9) . . ?
C2 N3 N2 109.0(9) . . ?
C2 N3 C5 128.1(8) . . ?
N2 N3 C5 121.9(8) . . ?
C3 N4 C4 112.7(7) . . ?
C3 N4 H4A 109.0 . . ?
C4 N4 H4A 109.0 . . ?
C3 N4 H4B 109.0 . . ?
C4 N4 H4B 109.0 . . ?
H4A N4 H4B 107.8 . . ?
N2 C1 N1 114.2(9) . . ?
N2 C1 C6 123.7(11) . . ?
N1 C1 C6 122.0(10) . . ?
N1 C2 N3 112.6(10) . . ?
N1 C2 C3 127.6(9) . . ?
N3 C2 C3 119.8(9) . . ?
N4 C3 C2 107.8(8) . . ?
N4 C3 C12 109.0(8) . . ?
C2 C3 C12 113.3(8) . . ?
N4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C12 C3 H3A 108.9 . . ?
C19A C4 N4 112.5(8) . . ?
C19 C4 N4 112.5(8) . . ?
C19A C4 C5 109.8(8) . . ?
C19 C4 C5 109.8(8) . . ?
N4 C4 C5 107.5(7) . . ?
C19 C4 H4 109.0 . . ?
N4 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
N3 C5 C4 109.6(8) . . ?
N3 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N3 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C11 118.9(11) . . ?
C7 C6 C1 119.7(12) . . ?
C11 C6 C1 121.4(11) . . ?
C6 C7 C8 120.4(15) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 120.6(15) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 119.0(14) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 120.1(15) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C6 C11 C10 120.9(14) . . ?
C6 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C3 115.5(9) . . ?
C13 C12 H12A 108.4 . . ?
C3 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C3 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C18 116.9(11) . . ?
C14 C13 C12 121.1(10) . . ?
C18 C13 C12 121.9(10) . . ?
C15 C14 C13 122.2(13) . . ?
C15 C14 H14A 118.9 . . ?
C13 C14 H14A 118.9 . . ?
C16 C15 C14 119.8(14) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C17 C16 C15 119.3(13) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 121.4(13) . . ?
C16 C17 H17A 119.3 . . ?
C18 C17 H17A 119.3 . . ?
C17 C18 C13 120.4(12) . . ?
C17 C18 H18A 119.8 . . ?
C13 C18 H18A 119.8 . . ?
C20 C19 C24 121.8(17) . . ?
C20 C19 C4 123.6(12) . . ?
C24 C19 C4 114.4(14) . . ?
C19 C20 C21 120.5(18) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 C20 122.7(19) . . ?
C22 C21 H21A 118.6 . . ?
C20 C21 H21A 118.6 . . ?
C21 C22 C23 115.9(15) . . ?
C21 C22 C25 124.0(14) . . ?
C23 C22 C25 119.8(14) . . ?
C24 C23 C22 120.3(19) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C19 C24 C23 118(2) . . ?
C19 C24 H24A 120.9 . . ?
C23 C24 H24A 120.9 . . ?
C24A C19A C4 122.4(14) . . ?
C24A C19A C20A 114.3(16) . . ?
C4 C19A C20A 123.2(12) . . ?
C21A C20A C19A 121.8(19) . . ?
C21A C20A H20B 119.1 . . ?
C19A C20A H20B 119.1 . . ?
C20A C21A C22A 115(2) . . ?
C20A C21A H21B 122.3 . . ?
C22A C21A H21B 122.3 . . ?
C23A C22A C21A 125.8(19) . . ?
C23A C22A C25 117.2(16) . . ?
C21A C22A C25 116.9(15) . . ?
C22A C23A C24A 120(2) . . ?
C22A C23A H23B 120.1 . . ?
C24A C23A H23B 120.1 . . ?
C23A C24A C19A 123(2) . . ?
C23A C24A H24B 118.6 . . ?
C19A C24A H24B 118.6 . . ?
F2 C25 F1 104.7(12) . . ?
F2 C25 F3 103.4(12) . . ?
F1 C25 F3 105.1(12) . . ?
F2 C25 C22A 115.3(12) . . ?
F1 C25 C22A 113.3(11) . . ?
F3 C25 C22A 113.9(11) . . ?
F2 C25 C22 115.3(12) . . ?
F1 C25 C22 113.3(11) . . ?
F3 C25 C22 113.9(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 -3.6(12) . . . . ?
C1 N2 N3 C5 -173.3(9) . . . . ?
N3 N2 C1 N1 2.7(12) . . . . ?
N3 N2 C1 C6 179.1(10) . . . . ?
C2 N1 C1 N2 -0.8(12) . . . . ?
C2 N1 C1 C6 -177.2(10) . . . . ?
C1 N1 C2 N3 -1.7(12) . . . . ?
C1 N1 C2 C3 -179.5(10) . . . . ?
N2 N3 C2 N1 3.5(13) . . . . ?
C5 N3 C2 N1 172.4(10) . . . . ?
N2 N3 C2 C3 -178.5(9) . . . . ?
C5 N3 C2 C3 -9.7(16) . . . . ?
C4 N4 C3 C2 -53.1(10) . . . . ?
C4 N4 C3 C12 -176.4(7) . . . . ?
N1 C2 C3 N4 -158.8(10) . . . . ?
N3 C2 C3 N4 23.5(13) . . . . ?
N1 C2 C3 C12 -38.2(15) . . . . ?
N3 C2 C3 C12 144.1(9) . . . . ?
C3 N4 C4 C19A -171.7(8) . . . . ?
C3 N4 C4 C19 -171.7(8) . . . . ?
C3 N4 C4 C5 67.3(10) . . . . ?
C2 N3 C5 C4 21.7(14) . . . . ?
N2 N3 C5 C4 -170.7(9) . . . . ?
C19A C4 C5 N3 -169.5(8) . . . . ?
C19 C4 C5 N3 -169.5(8) . . . . ?
N4 C4 C5 N3 -46.9(11) . . . . ?
N2 C1 C6 C7 -12.9(17) . . . . ?
N1 C1 C6 C7 163.1(11) . . . . ?
N2 C1 C6 C11 168.1(12) . . . . ?
N1 C1 C6 C11 -15.8(17) . . . . ?
C11 C6 C7 C8 1(2) . . . . ?
C1 C6 C7 C8 -178.0(14) . . . . ?
C6 C7 C8 C9 1(3) . . . . ?
C7 C8 C9 C10 -3(3) . . . . ?
C8 C9 C10 C11 3(3) . . . . ?
C7 C6 C11 C10 -1.3(19) . . . . ?
C1 C6 C11 C10 177.7(12) . . . . ?
C9 C10 C11 C6 -1(2) . . . . ?
N4 C3 C12 C13 -167.1(8) . . . . ?
C2 C3 C12 C13 73.0(11) . . . . ?
C3 C12 C13 C14 -127.7(11) . . . . ?
C3 C12 C13 C18 54.8(13) . . . . ?
C18 C13 C14 C15 -0.6(19) . . . . ?
C12 C13 C14 C15 -178.3(12) . . . . ?
C13 C14 C15 C16 0(2) . . . . ?
C14 C15 C16 C17 1(2) . . . . ?
C15 C16 C17 C18 0(2) . . . . ?
C16 C17 C18 C13 -1(2) . . . . ?
C14 C13 C18 C17 1.3(18) . . . . ?
C12 C13 C18 C17 178.9(11) . . . . ?
N4 C4 C19 C20 -12.9(19) . . . . ?
C5 C4 C19 C20 106.7(17) . . . . ?
N4 C4 C19 C24 163.2(16) . . . . ?
C5 C4 C19 C24 -77.1(17) . . . . ?
C24 C19 C20 C21 7(3) . . . . ?
C4 C19 C20 C21 -177.0(16) . . . . ?
C19 C20 C21 C22 -2(3) . . . . ?
C20 C21 C22 C23 -3(3) . . . . ?
C20 C21 C22 C25 -177.4(18) . . . . ?
C21 C22 C23 C24 4(3) . . . . ?
C25 C22 C23 C24 179(2) . . . . ?
C20 C19 C24 C23 -6(3) . . . . ?
C4 C19 C24 C23 178(2) . . . . ?
C22 C23 C24 C19 0(4) . . . . ?
N4 C4 C19A C24A 128.2(18) . . . . ?
C5 C4 C19A C24A -112.1(18) . . . . ?
N4 C4 C19A C20A -56.0(18) . . . . ?
C5 C4 C19A C20A 63.6(18) . . . . ?
C24A C19A C20A C21A 1(3) . . . . ?
C4 C19A C20A C21A -175(2) . . . . ?
C19A C20A C21A C22A -2(4) . . . . ?
C20A C21A C22A C23A 2(4) . . . . ?
C20A C21A C22A C25 -179(2) . . . . ?
C21A C22A C23A C24A -1(4) . . . . ?
C25 C22A C23A C24A 180(2) . . . . ?
C22A C23A C24A C19A 0(4) . . . . ?
C4 C19A C24A C23A 176(2) . . . . ?
C20A C19A C24A C23A 0(3) . . . . ?
C23A C22A C25 F2 -40(2) . . . . ?
C21A C22A C25 F2 140.0(18) . . . . ?
C23A C22A C25 F1 80(2) . . . . ?
C21A C22A C25 F1 -99(2) . . . . ?
C23A C22A C25 F3 -159(2) . . . . ?
C21A C22A C25 F3 21(2) . . . . ?
C21 C22 C25 F2 97.8(19) . . . . ?
C23 C22 C25 F2 -76(2) . . . . ?
C21 C22 C25 F1 -141.6(18) . . . . ?
C23 C22 C25 F1 44(2) . . . . ?
C21 C22 C25 F3 -22(2) . . . . ?
C23 C22 C25 F3 164.5(19) . . . . ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
