# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2091505'
loop_
_audit_author_name
_audit_author_address
'P. Anbarasan'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 N2, F6 Sb'

_chemical_formula_sum            'C23 H25 F6 N2 Sb'
_chemical_formula_weight         565.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1550(5)
_cell_length_b                   15.9851(10)
_cell_length_c                   18.1298(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.305(2)
_cell_angle_gamma                90
_cell_volume                     2309.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.00
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            green


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.256
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43544
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.308
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4052
_reflns_number_gt                2976
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.0401P)²+11.4700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4052
_refine_ls_number_parameters     350
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.13834(8) 0.80755(4) 0.55120(3) 0.0666(3) Uani 1 1 d D . . . .
F1 F 0.117(4) 0.890(2) 0.617(2) 0.151(13) Uani 0.497(19) 1 d D U P A 1
F2 F 0.111(4) 0.8969(12) 0.4862(12) 0.151(8) Uani 0.497(19) 1 d D U P A 1
F3 F 0.3629(19) 0.8300(18) 0.5748(19) 0.174(9) Uani 0.497(19) 1 d D U P A 1
F4 F 0.164(5) 0.7202(17) 0.4932(19) 0.199(12) Uani 0.497(19) 1 d D U P A 1
F5 F 0.148(4) 0.7348(16) 0.6267(13) 0.167(8) Uani 0.497(19) 1 d D U P A 1
F6 F -0.0945(15) 0.8025(12) 0.5346(15) 0.146(8) Uani 0.497(19) 1 d D U P A 1
F1' F 0.064(4) 0.866(2) 0.6219(18) 0.160(12) Uani 0.503(19) 1 d D U P A 2
F2' F 0.223(4) 0.8980(16) 0.5133(19) 0.208(11) Uani 0.503(19) 1 d D U P A 2
F3' F 0.340(2) 0.7903(15) 0.6206(13) 0.147(8) Uani 0.503(19) 1 d D U P A 2
F4' F 0.223(5) 0.7608(19) 0.4773(16) 0.206(13) Uani 0.503(19) 1 d D U P A 2
F5' F 0.092(4) 0.7067(12) 0.5870(15) 0.176(9) Uani 0.503(19) 1 d D U P A 2
F6' F -0.045(3) 0.8084(15) 0.4779(13) 0.172(9) Uani 0.503(19) 1 d D U P A 2
C1 C 0.6150(10) 0.4949(6) 0.4049(4) 0.062(2) Uani 1 1 d . . . . .
C2 C 0.7629(12) 0.5083(8) 0.4596(5) 0.086(3) Uani 1 1 d . . . . .
H2 H 0.850462 0.469984 0.465506 0.104 Uiso 1 1 calc R U . . .
C3 C 0.7767(14) 0.5763(9) 0.5029(6) 0.096(4) Uani 1 1 d . . . . .
H3 H 0.874629 0.584470 0.539249 0.115 Uiso 1 1 calc R U . . .
C4 C 0.6521(16) 0.6342(7) 0.4956(5) 0.090(4) Uani 1 1 d . . . . .
H4 H 0.666804 0.680779 0.527165 0.108 Uiso 1 1 calc R U . . .
C5 C 0.5007(12) 0.6252(6) 0.4412(5) 0.074(3) Uani 1 1 d . . . . .
H5 H 0.416717 0.665627 0.434267 0.089 Uiso 1 1 calc R U . . .
C6 C 0.4852(10) 0.5520(5) 0.3986(4) 0.056(2) Uani 1 1 d . . . . .
C7 C 0.5674(10) 0.4324(6) 0.3496(5) 0.063(2) Uani 1 1 d . . . . .
H7 H 0.633219 0.387105 0.341738 0.076 Uiso 1 1 calc R U . . .
C8 C 0.4123(9) 0.4487(5) 0.3103(4) 0.0506(18) Uani 1 1 d . . . . .
C9 C 0.2969(9) 0.4057(4) 0.2463(4) 0.0474(17) Uani 1 1 d . . . . .
C10 C 0.1726(9) 0.3429(5) 0.2726(4) 0.0543(19) Uani 1 1 d . . . . .
H10 H 0.131134 0.368302 0.314365 0.065 Uiso 1 1 calc R U . . .
C11 C 0.0299(10) 0.3409(4) 0.2029(4) 0.0533(19) Uani 1 1 d . . . . .
C12 C 0.0364(9) 0.4072(5) 0.1589(4) 0.0527(19) Uani 1 1 d . . . . .
C13 C 0.1745(8) 0.4663(4) 0.1963(4) 0.0432(16) Uani 1 1 d . . . . .
C14 C 0.2478(11) 0.5255(5) 0.1458(4) 0.063(2) Uani 1 1 d . . . . .
H14A H 0.283137 0.493939 0.106837 0.095 Uiso 1 1 calc R U . . .
H14B H 0.342506 0.554401 0.175411 0.095 Uiso 1 1 calc R U . . .
H14C H 0.164070 0.565385 0.123182 0.095 Uiso 1 1 calc R U . . .
C15 C 0.4066(11) 0.3611(5) 0.1984(5) 0.068(2) Uani 1 1 d . . . . .
H15A H 0.473241 0.401787 0.179026 0.103 Uiso 1 1 calc R U . . .
H15B H 0.335602 0.332415 0.157068 0.103 Uiso 1 1 calc R U . . .
H15C H 0.479029 0.321544 0.229229 0.103 Uiso 1 1 calc R U . . .
C16 C 0.2481(13) 0.2588(5) 0.2978(5) 0.080(3) Uani 1 1 d . . . . .
H16A H 0.175896 0.229449 0.324397 0.119 Uiso 1 1 calc R U . . .
H16B H 0.356175 0.266648 0.330543 0.119 Uiso 1 1 calc R U . . .
H16C H 0.260404 0.226915 0.254443 0.119 Uiso 1 1 calc R U . . .
C17 C -0.0971(12) 0.2735(6) 0.1919(6) 0.081(3) Uani 1 1 d . . . . .
H17A H -0.158259 0.275652 0.231641 0.122 Uiso 1 1 calc R U . . .
H17B H -0.042206 0.220236 0.192883 0.122 Uiso 1 1 calc R U . . .
H17C H -0.173300 0.280743 0.144100 0.122 Uiso 1 1 calc R U . . .
C18 C -0.0709(11) 0.4246(6) 0.0814(4) 0.081(3) Uani 1 1 d . . . . .
H18A H -0.180628 0.401202 0.078133 0.121 Uiso 1 1 calc R U . . .
H18B H -0.019951 0.399711 0.043647 0.121 Uiso 1 1 calc R U . . .
H18C H -0.080113 0.483928 0.073435 0.121 Uiso 1 1 calc R U . . .
C19 C 0.1932(9) 0.5499(4) 0.3192(4) 0.0445(17) Uani 1 1 d . . . . .
C20 C 0.1184(10) 0.6005(5) 0.3646(4) 0.058(2) Uani 1 1 d . . . . .
H20 H 0.180227 0.618005 0.411179 0.070 Uiso 1 1 calc R U . . .
C21 C -0.0428(12) 0.6248(5) 0.3421(5) 0.071(2) Uani 1 1 d . . . . .
H21 H -0.091742 0.658688 0.373077 0.085 Uiso 1 1 calc R U . . .
C22 C -0.1347(11) 0.5993(6) 0.2732(5) 0.077(3) Uani 1 1 d . . . . .
H22 H -0.245392 0.616412 0.256543 0.092 Uiso 1 1 calc R U . . .
C23 C -0.0594(11) 0.5482(5) 0.2295(5) 0.065(2) Uani 1 1 d . . . . .
H23 H -0.121745 0.529952 0.183267 0.078 Uiso 1 1 calc R U . . .
N1 N 0.3562(7) 0.5235(4) 0.3384(3) 0.0466(14) Uani 1 1 d . . . . .
N2 N 0.1028(7) 0.5233(3) 0.2514(3) 0.0438(14) 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
Sb1 F6' 1.778(11) . ?
Sb1 F5 1.786(14) . ?
Sb1 F4 1.788(12) . ?
Sb1 F1' 1.792(14) . ?
Sb1 F4' 1.797(16) . ?
Sb1 F2' 1.799(16) . ?
Sb1 F5' 1.809(14) . ?
Sb1 F1 1.811(13) . ?
Sb1 F3 1.825(14) . ?
Sb1 F2 1.834(13) . ?
Sb1 F6 1.860(12) . ?
Sb1 F3' 1.867(11) . ?
C1 C6 1.384(11) . ?
C1 C2 1.404(12) . ?
C1 C7 1.410(11) . ?
C2 C3 1.331(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(11) . ?
C5 H5 0.9300 . ?
C6 N1 1.419(9) . ?
C7 C8 1.339(10) . ?
C7 H7 0.9300 . ?
C8 N1 1.414(9) . ?
C8 C9 1.496(10) . ?
C9 C13 1.540(9) . ?
C9 C15 1.548(10) . ?
C9 C10 1.571(10) . ?
C10 C16 1.508(10) . ?
C10 C11 1.525(11) . ?
C10 H10 0.9800 . ?
C11 C12 1.334(10) . ?
C11 C17 1.479(10) . ?
C12 C18 1.513(10) . ?
C12 C13 1.516(9) . ?
C13 C14 1.525(9) . ?
C13 N2 1.554(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N2 1.361(8) . ?
C19 N1 1.367(9) . ?
C19 C20 1.385(10) . ?
C20 C21 1.348(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(11) . ?
C22 H22 0.9300 . ?
C23 N2 1.357(9) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F5 Sb1 F4 87.2(14) . . ?
F6' Sb1 F1' 99.9(15) . . ?
F6' Sb1 F4' 81.0(16) . . ?
F1' Sb1 F4' 173.0(17) . . ?
F6' Sb1 F2' 92.2(12) . . ?
F1' Sb1 F2' 93.9(18) . . ?
F4' Sb1 F2' 79.1(17) . . ?
F6' Sb1 F5' 93.8(11) . . ?
F1' Sb1 F5' 94.6(17) . . ?
F4' Sb1 F5' 92.3(14) . . ?
F2' Sb1 F5' 168.6(16) . . ?
F5 Sb1 F1 88.0(18) . . ?
F4 Sb1 F1 175(2) . . ?
F5 Sb1 F3 93.9(13) . . ?
F4 Sb1 F3 93.1(14) . . ?
F1 Sb1 F3 86.4(12) . . ?
F5 Sb1 F2 168.3(11) . . ?
F4 Sb1 F2 104.1(15) . . ?
F1 Sb1 F2 80.8(17) . . ?
F3 Sb1 F2 88.8(11) . . ?
F5 Sb1 F6 88.5(11) . . ?
F4 Sb1 F6 96.6(13) . . ?
F1 Sb1 F6 84.1(11) . . ?
F3 Sb1 F6 170.1(11) . . ?
F2 Sb1 F6 87.0(10) . . ?
F6' Sb1 F3' 170.4(10) . . ?
F1' Sb1 F3' 88.8(14) . . ?
F4' Sb1 F3' 90.9(15) . . ?
F2' Sb1 F3' 91.3(11) . . ?
F5' Sb1 F3' 81.3(10) . . ?
C6 C1 C2 119.0(9) . . ?
C6 C1 C7 108.6(7) . . ?
C2 C1 C7 132.4(10) . . ?
C3 C2 C1 119.5(11) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 122.1(10) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 121.4(10) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 115.8(10) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
C1 C6 C5 122.1(8) . . ?
C1 C6 N1 106.3(7) . . ?
C5 C6 N1 131.3(8) . . ?
C8 C7 C1 109.0(8) . . ?
C8 C7 H7 125.5 . . ?
C1 C7 H7 125.5 . . ?
C7 C8 N1 108.3(7) . . ?
C7 C8 C9 133.6(7) . . ?
N1 C8 C9 118.0(6) . . ?
C8 C9 C13 112.9(6) . . ?
C8 C9 C15 107.7(6) . . ?
C13 C9 C15 109.8(6) . . ?
C8 C9 C10 113.4(6) . . ?
C13 C9 C10 101.6(5) . . ?
C15 C9 C10 111.4(6) . . ?
C16 C10 C11 115.0(7) . . ?
C16 C10 C9 114.4(7) . . ?
C11 C10 C9 100.9(6) . . ?
C16 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
C12 C11 C17 127.9(8) . . ?
C12 C11 C10 111.0(6) . . ?
C17 C11 C10 121.0(7) . . ?
C11 C12 C18 127.8(7) . . ?
C11 C12 C13 110.4(6) . . ?
C18 C12 C13 121.9(7) . . ?
C12 C13 C14 117.8(6) . . ?
C12 C13 C9 101.4(6) . . ?
C14 C13 C9 117.1(6) . . ?
C12 C13 N2 107.9(5) . . ?
C14 C13 N2 105.8(5) . . ?
C9 C13 N2 106.0(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 N1 116.4(6) . . ?
N2 C19 C20 119.8(7) . . ?
N1 C19 C20 123.8(7) . . ?
C21 C20 C19 120.9(8) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.8(8) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 118.5(8) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
N2 C23 C22 122.3(8) . . ?
N2 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C19 N1 C8 122.7(6) . . ?
C19 N1 C6 128.2(6) . . ?
C8 N1 C6 107.8(6) . . ?
C23 N2 C19 118.6(6) . . ?
C23 N2 C13 117.5(6) . . ?
C19 N2 C13 123.9(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
C6 C1 C2 C3 -1.5(13) . . . . ?
C7 C1 C2 C3 176.6(9) . . . . ?
C1 C2 C3 C4 -0.6(15) . . . . ?
C2 C3 C4 C5 -0.2(16) . . . . ?
C3 C4 C5 C6 2.9(13) . . . . ?
C2 C1 C6 C5 4.4(12) . . . . ?
C7 C1 C6 C5 -174.1(7) . . . . ?
C2 C1 C6 N1 178.6(7) . . . . ?
C7 C1 C6 N1 0.2(9) . . . . ?
C4 C5 C6 C1 -4.9(12) . . . . ?
C4 C5 C6 N1 -177.6(8) . . . . ?
C6 C1 C7 C8 -0.8(9) . . . . ?
C2 C1 C7 C8 -179.0(9) . . . . ?
C1 C7 C8 N1 1.1(9) . . . . ?
C1 C7 C8 C9 -179.6(8) . . . . ?
C7 C8 C9 C13 -151.9(8) . . . . ?
N1 C8 C9 C13 27.4(9) . . . . ?
C7 C8 C9 C15 -30.5(12) . . . . ?
N1 C8 C9 C15 148.8(6) . . . . ?
C7 C8 C9 C10 93.2(10) . . . . ?
N1 C8 C9 C10 -87.5(8) . . . . ?
C8 C9 C10 C16 -80.5(8) . . . . ?
C13 C9 C10 C16 158.1(7) . . . . ?
C15 C9 C10 C16 41.2(9) . . . . ?
C8 C9 C10 C11 155.5(6) . . . . ?
C13 C9 C10 C11 34.0(6) . . . . ?
C15 C9 C10 C11 -82.8(7) . . . . ?
C16 C10 C11 C12 -142.5(7) . . . . ?
C9 C10 C11 C12 -18.9(8) . . . . ?
C16 C10 C11 C17 39.7(11) . . . . ?
C9 C10 C11 C17 163.3(7) . . . . ?
C17 C11 C12 C18 -8.7(14) . . . . ?
C10 C11 C12 C18 173.7(8) . . . . ?
C17 C11 C12 C13 172.6(7) . . . . ?
C10 C11 C12 C13 -5.0(9) . . . . ?
C11 C12 C13 C14 156.5(7) . . . . ?
C18 C12 C13 C14 -22.3(10) . . . . ?
C11 C12 C13 C9 27.3(8) . . . . ?
C18 C12 C13 C9 -151.5(7) . . . . ?
C11 C12 C13 N2 -83.9(7) . . . . ?
C18 C12 C13 N2 97.3(8) . . . . ?
C8 C9 C13 C12 -158.7(6) . . . . ?
C15 C9 C13 C12 81.1(7) . . . . ?
C10 C9 C13 C12 -36.9(6) . . . . ?
C8 C9 C13 C14 71.6(8) . . . . ?
C15 C9 C13 C14 -48.5(8) . . . . ?
C10 C9 C13 C14 -166.5(6) . . . . ?
C8 C9 C13 N2 -46.1(7) . . . . ?
C15 C9 C13 N2 -166.3(6) . . . . ?
C10 C9 C13 N2 75.7(6) . . . . ?
N2 C19 C20 C21 -0.8(11) . . . . ?
N1 C19 C20 C21 179.5(7) . . . . ?
C19 C20 C21 C22 -0.2(13) . . . . ?
C20 C21 C22 C23 1.1(14) . . . . ?
C21 C22 C23 N2 -1.2(14) . . . . ?
N2 C19 N1 C8 -26.3(9) . . . . ?
C20 C19 N1 C8 153.4(7) . . . . ?
N2 C19 N1 C6 168.7(6) . . . . ?
C20 C19 N1 C6 -11.6(11) . . . . ?
C7 C8 N1 C19 -168.6(7) . . . . ?
C9 C8 N1 C19 11.9(10) . . . . ?
C7 C8 N1 C6 -1.0(8) . . . . ?
C9 C8 N1 C6 179.6(6) . . . . ?
C1 C6 N1 C19 167.3(7) . . . . ?
C5 C6 N1 C19 -19.2(13) . . . . ?
C1 C6 N1 C8 0.5(8) . . . . ?
C5 C6 N1 C8 174.0(8) . . . . ?
C22 C23 N2 C19 0.3(12) . . . . ?
C22 C23 N2 C13 -179.1(7) . . . . ?
N1 C19 N2 C23 -179.6(6) . . . . ?
C20 C19 N2 C23 0.7(10) . . . . ?
N1 C19 N2 C13 -0.2(9) . . . . ?
C20 C19 N2 C13 -179.9(6) . . . . ?
C12 C13 N2 C23 -37.0(8) . . . . ?
C14 C13 N2 C23 90.0(7) . . . . ?
C9 C13 N2 C23 -145.0(6) . . . . ?
C12 C13 N2 C19 143.6(6) . . . . ?
C14 C13 N2 C19 -89.4(7) . . . . ?
C9 C13 N2 C19 35.6(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 F4'^b 0.93 2.44 3.30(3) 154.0 . yes
C7 H7 F5^a 0.93 2.62 3.50(2) 158.9 3_666 yes
C14 H14A F2^a 0.96 2.57 3.530(16) 173.6 2_545 yes
C14 H14B F1'^b 0.96 2.56 3.21(3) 125.1 4_675 yes
C20 H20 F4^a 0.93 2.23 2.977(18) 136.7 . yes
C20 H20 F4'^b 0.93 2.57 3.28(3) 133.3 . yes
C22 H22 F1^a 0.93 2.54 3.12(3) 120.3 4_575 yes
C22 H22 F1'^b 0.93 2.61 3.31(4) 132.6 4_575 yes
C23 H23 F1^a 0.93 2.56 3.13(3) 120.5 4_575 yes

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.111



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
