# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1888935'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01359 Ang.  
RESPONSE: It is possible that the partial occupancy of the DCM molecule 
along a four-fold screw axis influences the displacement parameters of 
the cation resulting in increased uncertainty in the position of the 
atoms. 
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'1,3-dimethyl-4,5-bis(2-methyl-5-(4-vinylphenyl)thiophen-3-yl)-1H-imidazol-3-ium hexafluorophosphate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H29 N2 S2, P F6, 1/4 C H2 Cl2'
_chemical_formula_sum            'C31.25 H29.50 Cl0.50 F6 N2 P S2'
_chemical_formula_weight         659.88

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'

_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'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   39.9997(16)
_cell_length_b                   39.9997(16)
_cell_length_c                   7.8237(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12517.7(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3152
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      54.2

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             5448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.953
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Agilent SuperNova with Atlas S2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17609
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.494
_diffrn_reflns_theta_max         69.968
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.825
_reflns_number_total             4848
_reflns_number_gt                3418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.514
_reflns_Friedel_fraction_max     0.604
_reflns_Friedel_fraction_full    0.621

_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       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'





_refine_special_details          
;
 A molecule of DCM was observed in a difference electron density map.  However, 
the electron density associated with this molecule indicated that it was 
partially occupied.  The site occupancy was estimated to be about 25%.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+28.1826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 851 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4848
_refine_ls_number_parameters     410
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

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 0.7378(3) 0.2298(3) 0.9693(19) 0.080(4) Uani 0.25 1 d D U P A -1
Cl2 Cl 0.7604(3) 0.2466(4) 1.3121(17) 0.079(4) Uani 0.25 1 d D U P A -1
C1A C 0.7725(5) 0.2411(11) 1.097(3) 0.065(12) Uani 0.25 1 d D U P A -1
H1A1 H 0.7897 0.2233 1.0899 0.078 Uiso 0.25 1 calc R U P A -1
H1A2 H 0.7824 0.2621 1.0530 0.078 Uiso 0.25 1 calc R U P A -1
C1 C 0.6654(2) 0.4212(2) 1.0282(12) 0.056(2) Uani 1 1 d . . . . .
C2 C 0.6436(2) 0.4271(2) 0.8987(10) 0.044(2) Uani 1 1 d . . . . .
C3 C 0.6598(2) 0.4378(2) 0.7468(11) 0.047(2) Uani 1 1 d . . . . .
H3 H 0.6481 0.4429 0.6445 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6935(2) 0.4403(2) 0.7607(11) 0.048(2) Uani 1 1 d . . . . .
C5 C 0.7189(2) 0.44851(19) 0.6294(11) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.7519(2) 0.4383(2) 0.6476(13) 0.057(2) Uani 1 1 d . . . . .
H6 H 0.7584 0.4263 0.7470 0.069 Uiso 1 1 calc R U . . .
C7 C 0.7756(3) 0.4454(2) 0.5242(14) 0.065(3) Uani 1 1 d . . . . .
H7 H 0.7979 0.4379 0.5390 0.078 Uiso 1 1 calc R U . . .
C8 C 0.7669(3) 0.4634(2) 0.3773(13) 0.061(3) Uani 1 1 d . . . . .
C9 C 0.7341(2) 0.4734(2) 0.3641(12) 0.057(3) Uani 1 1 d . . . . .
H9 H 0.7275 0.4855 0.2653 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7105(2) 0.4668(2) 0.4864(12) 0.053(2) Uani 1 1 d . . . . .
H10 H 0.6883 0.4748 0.4726 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7900(3) 0.4711(3) 0.238(2) 0.092(4) Uani 1 1 d . . . . .
H11 H 0.7814 0.4838 0.1451 0.110 Uiso 1 1 calc R U . . .
C12 C 0.8193(4) 0.4630(3) 0.229(2) 0.104(5) Uani 1 1 d . . . . .
H12A H 0.8292 0.4503 0.3188 0.124 Uiso 1 1 calc R U . . .
H12B H 0.8323 0.4692 0.1328 0.124 Uiso 1 1 calc R U . . .
C13 C 0.6588(3) 0.4089(3) 1.2055(12) 0.071(3) Uani 1 1 d . . . . .
H13A H 0.6367 0.4165 1.2429 0.106 Uiso 1 1 calc R U . . .
H13B H 0.6759 0.4176 1.2832 0.106 Uiso 1 1 calc R U . . .
H13C H 0.6595 0.3844 1.2065 0.106 Uiso 1 1 calc R U . . .
C14 C 0.6078(2) 0.4191(2) 0.9116(10) 0.044(2) Uani 1 1 d . . . . .
C15 C 0.5934(2) 0.38946(19) 0.9382(10) 0.0372(18) Uani 1 1 d . . . . .
C16 C 0.5530(2) 0.4271(2) 0.9301(11) 0.046(2) Uani 1 1 d . . . . .
H16 H 0.5318 0.4377 0.9333 0.055 Uiso 1 1 calc R U . . .
C17 C 0.5856(2) 0.4784(2) 0.8832(12) 0.060(3) Uani 1 1 d . . . . .
H17A H 0.5878 0.4835 0.7612 0.090 Uiso 1 1 calc R U . . .
H17B H 0.6057 0.4861 0.9436 0.090 Uiso 1 1 calc R U . . .
H17C H 0.5659 0.4899 0.9296 0.090 Uiso 1 1 calc R U . . .
C18 C 0.53350(19) 0.3690(2) 0.9703(12) 0.052(2) Uani 1 1 d . . . . .
H18A H 0.5134 0.3791 1.0199 0.077 Uiso 1 1 calc R U . . .
H18B H 0.5419 0.3515 1.0465 0.077 Uiso 1 1 calc R U . . .
H18C H 0.5281 0.3593 0.8587 0.077 Uiso 1 1 calc R U . . .
C19 C 0.6256(2) 0.3427(2) 0.8134(12) 0.052(2) Uani 1 1 d . . . . .
C20 C 0.60872(19) 0.3559(2) 0.9477(11) 0.044(2) Uani 1 1 d . . . . .
C21 C 0.6101(2) 0.3359(2) 1.0981(11) 0.045(2) Uani 1 1 d . . . . .
H21 H 0.5997 0.3419 1.2028 0.054 Uiso 1 1 calc R U . . .
C22 C 0.6282(2) 0.3069(2) 1.0760(11) 0.048(2) Uani 1 1 d . . . . .
C23 C 0.6355(2) 0.2812(2) 1.2053(14) 0.052(2) Uani 1 1 d . . . . .
C24 C 0.6182(2) 0.2795(2) 1.3578(13) 0.054(2) Uani 1 1 d . . . . .
H24 H 0.6002 0.2945 1.3758 0.065 Uiso 1 1 calc R U . . .
C25 C 0.6261(3) 0.2571(2) 1.4845(14) 0.066(3) Uani 1 1 d . . . . .
H25 H 0.6133 0.2568 1.5869 0.080 Uiso 1 1 calc R U . . .
C26 C 0.6525(3) 0.2348(2) 1.4649(15) 0.070(3) Uani 1 1 d . . . . .
C27 C 0.6691(3) 0.2354(3) 1.3076(15) 0.074(3) Uani 1 1 d . . . . .
H27 H 0.6865 0.2198 1.2876 0.089 Uiso 1 1 calc R U . . .
C28 C 0.6610(3) 0.2579(2) 1.1803(15) 0.069(3) Uani 1 1 d . . . . .
H28 H 0.6729 0.2576 1.0752 0.083 Uiso 1 1 calc R U . . .
C29 C 0.6628(4) 0.2127(3) 1.6054(16) 0.095(4) Uani 1 1 d . . . . .
H29 H 0.6788 0.1960 1.5764 0.114 Uiso 1 1 calc R U . . .
C30 C 0.6532(4) 0.2129(3) 1.7630(17) 0.096(4) Uani 1 1 d . . . . .
H30A H 0.6373 0.2290 1.8006 0.115 Uiso 1 1 calc R U . . .
H30B H 0.6620 0.1970 1.8414 0.115 Uiso 1 1 calc R U . . .
C31 C 0.6292(2) 0.3561(2) 0.6350(13) 0.063(3) Uani 1 1 d . . . . .
H31A H 0.6099 0.3702 0.6074 0.094 Uiso 1 1 calc R U . . .
H31B H 0.6304 0.3374 0.5541 0.094 Uiso 1 1 calc R U . . .
H31C H 0.6497 0.3694 0.6271 0.094 Uiso 1 1 calc R U . . .
N1 N 0.58189(19) 0.44218(16) 0.9063(9) 0.0467(18) Uani 1 1 d . . . . .
N2 N 0.55873(17) 0.39434(16) 0.9493(8) 0.0422(16) Uani 1 1 d . . . . .
F1 F 0.53842(14) 0.45534(13) 0.5167(7) 0.0713(16) Uani 1 1 d . . . . .
F2 F 0.52458(12) 0.41704(14) 0.3176(6) 0.0667(15) Uani 1 1 d . . . . .
F3 F 0.57634(13) 0.39535(12) 0.3309(6) 0.0599(14) Uani 1 1 d . . . . .
F4 F 0.59051(12) 0.43368(14) 0.5294(6) 0.0686(16) Uani 1 1 d . . . . .
F5 F 0.54579(13) 0.40043(12) 0.5715(6) 0.0593(14) Uani 1 1 d . . . . .
F6 F 0.56951(14) 0.44996(12) 0.2743(6) 0.0629(15) Uani 1 1 d . . . . .
P1 P 0.55739(6) 0.42539(6) 0.4238(3) 0.0469(5) Uani 1 1 d . . . . .
S1 S 0.70616(6) 0.42866(7) 0.9654(3) 0.0623(7) Uani 1 1 d . . . . .
S2 S 0.64357(6) 0.30484(6) 0.8698(3) 0.0539(6) 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
Cl1 C1A 1.766(13) . ?
Cl2 C1A 1.766(13) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C1 C2 1.358(11) . ?
C1 C13 1.496(12) . ?
C1 S1 1.728(9) . ?
C2 C3 1.421(11) . ?
C2 C14 1.469(11) . ?
C3 C4 1.355(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.480(12) . ?
C4 S1 1.743(9) . ?
C5 C10 1.378(12) . ?
C5 C6 1.390(12) . ?
C6 C7 1.380(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(13) . ?
C8 C11 1.463(16) . ?
C9 C10 1.370(12) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.218(15) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.336(10) . ?
C14 N1 1.389(10) . ?
C15 N2 1.404(10) . ?
C15 C20 1.477(10) . ?
C16 N1 1.315(10) . ?
C16 N2 1.338(10) . ?
C16 H16 0.9500 . ?
C17 N1 1.469(10) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N2 1.439(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.356(11) . ?
C19 C31 1.501(12) . ?
C19 S2 1.733(9) . ?
C20 C21 1.425(11) . ?
C21 C22 1.376(11) . ?
C21 H21 0.9500 . ?
C22 C23 1.473(12) . ?
C22 S2 1.729(9) . ?
C23 C24 1.381(13) . ?
C23 C28 1.392(12) . ?
C24 C25 1.374(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.398(15) . ?
C26 C29 1.470(14) . ?
C27 C28 1.381(13) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.293(16) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9500 . ?
C30 H30B 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
F1 P1 1.594(5) . ?
F2 P1 1.589(5) . ?
F3 P1 1.596(5) . ?
F4 P1 1.597(5) . ?
F5 P1 1.596(5) . ?
F6 P1 1.603(5) . ?

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
Cl2 C1A Cl1 110.8(10) . . ?
Cl2 C1A H1A1 109.5 . . ?
Cl1 C1A H1A1 109.5 . . ?
Cl2 C1A H1A2 109.5 . . ?
Cl1 C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 108.1 . . ?
C2 C1 C13 129.4(8) . . ?
C2 C1 S1 111.3(7) . . ?
C13 C1 S1 119.2(7) . . ?
C1 C2 C3 112.5(8) . . ?
C1 C2 C14 122.5(8) . . ?
C3 C2 C14 124.6(7) . . ?
C4 C3 C2 114.2(8) . . ?
C4 C3 H3 122.9 . . ?
C2 C3 H3 122.9 . . ?
C3 C4 C5 129.9(8) . . ?
C3 C4 S1 110.0(7) . . ?
C5 C4 S1 119.9(7) . . ?
C10 C5 C6 118.0(9) . . ?
C10 C5 C4 121.0(9) . . ?
C6 C5 C4 121.0(8) . . ?
C7 C6 C5 121.3(10) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.6(10) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 116.6(9) . . ?
C9 C8 C11 119.0(11) . . ?
C7 C8 C11 124.3(11) . . ?
C10 C9 C8 123.2(9) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C10 C5 120.2(9) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C12 C11 C8 126.4(15) . . ?
C12 C11 H11 116.8 . . ?
C8 C11 H11 116.8 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N1 105.8(8) . . ?
C15 C14 C2 128.6(8) . . ?
N1 C14 C2 125.6(7) . . ?
C14 C15 N2 108.2(7) . . ?
C14 C15 C20 129.5(8) . . ?
N2 C15 C20 122.2(7) . . ?
N1 C16 N2 108.4(7) . . ?
N1 C16 H16 125.8 . . ?
N2 C16 H16 125.8 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C31 129.0(8) . . ?
C20 C19 S2 110.4(7) . . ?
C31 C19 S2 120.5(7) . . ?
C19 C20 C21 113.7(7) . . ?
C19 C20 C15 121.4(8) . . ?
C21 C20 C15 124.7(7) . . ?
C22 C21 C20 113.0(8) . . ?
C22 C21 H21 123.5 . . ?
C20 C21 H21 123.5 . . ?
C21 C22 C23 127.4(8) . . ?
C21 C22 S2 110.1(7) . . ?
C23 C22 S2 122.4(6) . . ?
C24 C23 C28 117.1(9) . . ?
C24 C23 C22 121.7(8) . . ?
C28 C23 C22 121.1(9) . . ?
C25 C24 C23 122.7(9) . . ?
C25 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C24 C25 C26 120.9(10) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C27 116.4(10) . . ?
C25 C26 C29 121.2(11) . . ?
C27 C26 C29 122.4(10) . . ?
C28 C27 C26 122.4(10) . . ?
C28 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C27 C28 C23 120.3(10) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C30 C29 C26 128.7(13) . . ?
C30 C29 H29 115.7 . . ?
C26 C29 H29 115.7 . . ?
C29 C30 H30A 120.0 . . ?
C29 C30 H30B 120.0 . . ?
H30A C30 H30B 120.0 . . ?
C19 C31 H31A 109.5 . . ?
C19 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C19 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C16 N1 C14 110.3(7) . . ?
C16 N1 C17 124.0(7) . . ?
C14 N1 C17 125.7(8) . . ?
C16 N2 C15 107.3(7) . . ?
C16 N2 C18 125.6(7) . . ?
C15 N2 C18 127.0(7) . . ?
F2 P1 F1 90.2(3) . . ?
F2 P1 F3 89.8(3) . . ?
F1 P1 F3 179.9(4) . . ?
F2 P1 F5 90.4(3) . . ?
F1 P1 F5 90.1(3) . . ?
F3 P1 F5 89.8(3) . . ?
F2 P1 F4 179.6(4) . . ?
F1 P1 F4 90.1(3) . . ?
F3 P1 F4 89.9(3) . . ?
F5 P1 F4 89.8(3) . . ?
F2 P1 F6 89.8(3) . . ?
F1 P1 F6 90.9(3) . . ?
F3 P1 F6 89.2(3) . . ?
F5 P1 F6 179.0(3) . . ?
F4 P1 F6 90.0(3) . . ?
C1 S1 C4 92.0(5) . . ?
C22 S2 C19 92.8(4) . . ?

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
C13 C1 C2 C3 -178.2(9) . . . . ?
S1 C1 C2 C3 -0.3(10) . . . . ?
C13 C1 C2 C14 -4.9(15) . . . . ?
S1 C1 C2 C14 173.0(6) . . . . ?
C1 C2 C3 C4 -0.3(11) . . . . ?
C14 C2 C3 C4 -173.4(8) . . . . ?
C2 C3 C4 C5 175.8(8) . . . . ?
C2 C3 C4 S1 0.7(9) . . . . ?
C3 C4 C5 C10 24.5(13) . . . . ?
S1 C4 C5 C10 -160.8(6) . . . . ?
C3 C4 C5 C6 -156.2(9) . . . . ?
S1 C4 C5 C6 18.5(11) . . . . ?
C10 C5 C6 C7 -2.0(13) . . . . ?
C4 C5 C6 C7 178.7(8) . . . . ?
C5 C6 C7 C8 0.8(14) . . . . ?
C6 C7 C8 C9 -0.1(13) . . . . ?
C6 C7 C8 C11 -178.1(9) . . . . ?
C7 C8 C9 C10 0.6(13) . . . . ?
C11 C8 C9 C10 178.7(9) . . . . ?
C8 C9 C10 C5 -1.8(13) . . . . ?
C6 C5 C10 C9 2.4(12) . . . . ?
C4 C5 C10 C9 -178.3(7) . . . . ?
C9 C8 C11 C12 -177.4(12) . . . . ?
C7 C8 C11 C12 0.6(19) . . . . ?
C1 C2 C14 C15 -60.3(13) . . . . ?
C3 C2 C14 C15 112.1(10) . . . . ?
C1 C2 C14 N1 116.3(10) . . . . ?
C3 C2 C14 N1 -71.2(12) . . . . ?
N1 C14 C15 N2 -0.1(9) . . . . ?
C2 C14 C15 N2 177.1(8) . . . . ?
N1 C14 C15 C20 177.1(8) . . . . ?
C2 C14 C15 C20 -5.8(14) . . . . ?
C31 C19 C20 C21 178.7(9) . . . . ?
S2 C19 C20 C21 0.4(10) . . . . ?
C31 C19 C20 C15 -6.8(14) . . . . ?
S2 C19 C20 C15 174.8(6) . . . . ?
C14 C15 C20 C19 -60.7(12) . . . . ?
N2 C15 C20 C19 116.1(9) . . . . ?
C14 C15 C20 C21 113.1(10) . . . . ?
N2 C15 C20 C21 -70.1(10) . . . . ?
C19 C20 C21 C22 -0.7(11) . . . . ?
C15 C20 C21 C22 -174.9(8) . . . . ?
C20 C21 C22 C23 177.9(8) . . . . ?
C20 C21 C22 S2 0.6(9) . . . . ?
C21 C22 C23 C24 15.7(14) . . . . ?
S2 C22 C23 C24 -167.4(7) . . . . ?
C21 C22 C23 C28 -162.7(9) . . . . ?
S2 C22 C23 C28 14.3(12) . . . . ?
C28 C23 C24 C25 2.6(14) . . . . ?
C22 C23 C24 C25 -175.8(8) . . . . ?
C23 C24 C25 C26 0.5(15) . . . . ?
C24 C25 C26 C27 -3.2(16) . . . . ?
C24 C25 C26 C29 174.7(10) . . . . ?
C25 C26 C27 C28 3.0(17) . . . . ?
C29 C26 C27 C28 -174.9(10) . . . . ?
C26 C27 C28 C23 0.0(17) . . . . ?
C24 C23 C28 C27 -2.8(14) . . . . ?
C22 C23 C28 C27 175.6(9) . . . . ?
C25 C26 C29 C30 -9(2) . . . . ?
C27 C26 C29 C30 168.9(14) . . . . ?
N2 C16 N1 C14 -0.8(10) . . . . ?
N2 C16 N1 C17 -178.9(7) . . . . ?
C15 C14 N1 C16 0.5(9) . . . . ?
C2 C14 N1 C16 -176.8(8) . . . . ?
C15 C14 N1 C17 178.6(7) . . . . ?
C2 C14 N1 C17 1.4(13) . . . . ?
N1 C16 N2 C15 0.7(9) . . . . ?
N1 C16 N2 C18 -177.0(8) . . . . ?
C14 C15 N2 C16 -0.4(9) . . . . ?
C20 C15 N2 C16 -177.8(7) . . . . ?
C14 C15 N2 C18 177.3(8) . . . . ?
C20 C15 N2 C18 -0.1(12) . . . . ?
C2 C1 S1 C4 0.6(7) . . . . ?
C13 C1 S1 C4 178.7(8) . . . . ?
C3 C4 S1 C1 -0.7(7) . . . . ?
C5 C4 S1 C1 -176.4(7) . . . . ?
C21 C22 S2 C19 -0.3(7) . . . . ?
C23 C22 S2 C19 -177.7(7) . . . . ?
C20 C19 S2 C22 0.0(7) . . . . ?
C31 C19 S2 C22 -178.5(8) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
