# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1a_PF6
_database_code_depnum_ccdc_archive 'CCDC 1476623'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
;
1-benzyl-3-iodopyridinium hexafluorophosphate
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 I N, F6 P'
_chemical_formula_sum            'C12 H11 F6 I N P'
_chemical_formula_weight         441.09

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'
I I -0.4742 1.8119 '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'
P P 0.1023 0.0942 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2557(10)
_cell_length_b                   9.7230(18)
_cell_length_c                   15.2850(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.674(9)
_cell_angle_gamma                90
_cell_volume                     1513.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8
_cell_measurement_theta_max      13

_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  300
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3500
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         26.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3289
_reflns_number_gt                2298
_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0465P)²+3.6648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         3289
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_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
I1 I 0.01719(5) 0.11958(8) 0.79660(3) 0.1098(3) Uani 1 1 d . . . . .
C1 C -0.1371(7) 0.1090(8) 0.6948(4) 0.0739(19) Uani 1 1 d . . . . .
C2 C -0.1312(7) 0.1896(8) 0.6208(4) 0.0721(18) Uani 1 1 d . . . . .
H2 H -0.0570 0.2428 0.6157 0.087 Uiso 1 1 calc R U . . .
C3 C -0.3388(7) 0.1163(7) 0.5627(4) 0.0708(17) Uani 1 1 d . . . . .
H3 H -0.4077 0.1188 0.5174 0.085 Uiso 1 1 calc R U . . .
C4 C -0.3476(8) 0.0358(8) 0.6352(4) 0.081(2) Uani 1 1 d . . . . .
H4 H -0.4229 -0.0160 0.6392 0.097 Uiso 1 1 calc R U . . .
C5 C -0.2465(8) 0.0310(8) 0.7016(5) 0.079(2) Uani 1 1 d . . . . .
H5 H -0.2519 -0.0244 0.7507 0.094 Uiso 1 1 calc R U . . .
C6 C -0.2239(10) 0.2881(10) 0.4809(5) 0.109(3) Uani 1 1 d . . . . .
H6A H -0.1328 0.2998 0.4711 0.131 Uiso 1 1 calc R U . . .
H6B H -0.2572 0.3773 0.4961 0.131 Uiso 1 1 calc R U . . .
C7 C -0.3008(7) 0.2389(7) 0.3969(4) 0.0679(17) Uani 1 1 d . . . . .
C8 C -0.4187(7) 0.3006(7) 0.3660(5) 0.0756(18) Uani 1 1 d . . . . .
H8 H -0.4525 0.3701 0.3986 0.091 Uiso 1 1 calc R U . . .
C9 C -0.4860(7) 0.2597(8) 0.2873(5) 0.080(2) Uani 1 1 d . . . . .
H9 H -0.5652 0.3014 0.2666 0.096 Uiso 1 1 calc R U . . .
C10 C -0.4368(8) 0.1587(8) 0.2402(5) 0.081(2) Uani 1 1 d . . . . .
H10 H -0.4828 0.1319 0.1869 0.097 Uiso 1 1 calc R U . . .
C11 C -0.3230(8) 0.0958(8) 0.2683(6) 0.083(2) Uani 1 1 d . . . . .
H11 H -0.2899 0.0270 0.2348 0.099 Uiso 1 1 calc R U . . .
C12 C -0.2560(7) 0.1354(8) 0.3479(6) 0.084(2) Uani 1 1 d . . . . .
H12 H -0.1785 0.0904 0.3687 0.100 Uiso 1 1 calc R U . . .
N1 N -0.2306(5) 0.1915(6) 0.5571(3) 0.0666(14) Uani 1 1 d . . . . .
F1 F 0.2602(6) 0.2073(11) 0.9337(4) 0.184(3) Uani 1 1 d . . . . .
F2 F 0.1219(6) 0.1258(6) 1.0187(5) 0.141(2) Uani 1 1 d . . . . .
F3 F 0.3403(7) 0.1121(6) 1.0588(6) 0.185(4) Uani 1 1 d . . . . .
F4 F 0.3575(5) 0.3331(6) 1.0425(4) 0.1285(19) Uani 1 1 d . . . . .
F5 F 0.2223(8) 0.2529(9) 1.1283(4) 0.176(3) Uani 1 1 d . . . . .
F6 F 0.1424(6) 0.3436(6) 1.0035(5) 0.157(3) Uani 1 1 d . . . . .
P1 P 0.24180(18) 0.2276(2) 1.03042(13) 0.0712(5) 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
I1 C1 2.089(7) . ?
C1 C5 1.368(10) . ?
C1 C2 1.384(9) . ?
C2 N1 1.325(8) . ?
C2 H2 0.9300 . ?
C3 N1 1.340(8) . ?
C3 C4 1.368(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(10) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 N1 1.504(9) . ?
C6 C7 1.505(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.365(10) . ?
C7 C8 1.383(10) . ?
C8 C9 1.375(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.350(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.343(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
F1 P1 1.525(6) . ?
F2 P1 1.573(5) . ?
F3 P1 1.539(5) . ?
F4 P1 1.562(5) . ?
F5 P1 1.552(6) . ?
F6 P1 1.544(6) . ?

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
C5 C1 C2 119.4(7) . . ?
C5 C1 I1 121.8(5) . . ?
C2 C1 I1 118.6(6) . . ?
N1 C2 C1 120.3(7) . . ?
N1 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
N1 C3 C4 119.8(7) . . ?
N1 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C1 118.8(6) . . ?
C4 C5 H5 120.6 . . ?
C1 C5 H5 120.6 . . ?
N1 C6 C7 113.3(6) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C12 C7 C8 118.0(7) . . ?
C12 C7 C6 121.7(8) . . ?
C8 C7 C6 120.2(8) . . ?
C9 C8 C7 120.2(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.7(7) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 121.7(7) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 118.7(8) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C7 C12 C11 121.6(7) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C2 N1 C3 121.2(6) . . ?
C2 N1 C6 118.5(6) . . ?
C3 N1 C6 120.2(6) . . ?
F1 P1 F3 91.5(5) . . ?
F1 P1 F6 89.4(5) . . ?
F3 P1 F6 179.1(5) . . ?
F1 P1 F5 178.3(5) . . ?
F3 P1 F5 89.9(5) . . ?
F6 P1 F5 89.2(5) . . ?
F1 P1 F4 91.3(4) . . ?
F3 P1 F4 88.9(4) . . ?
F6 P1 F4 91.2(3) . . ?
F5 P1 F4 87.9(4) . . ?
F1 P1 F2 89.5(4) . . ?
F3 P1 F2 92.9(4) . . ?
F6 P1 F2 86.9(3) . . ?
F5 P1 F2 91.3(4) . . ?
F4 P1 F2 178.0(4) . . ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.082

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetonitrile
####################################################################### 
# 
# 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_1a_I
_database_code_depnum_ccdc_archive 'CCDC 1476624'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
;
bis(1-benzyl-3-iodopyridinium iodide)
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H11 I N), 2(I)'
_chemical_formula_sum            'C24 H22 I4 N2'
_chemical_formula_weight         846.04

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c 21 b'
_symmetry_space_group_name_Hall  'P -2bc -2c'
_symmetry_Int_Tables_number      29

_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'
'-x, y, z+1/2'
'x, y+1/2, -z+1/2'

_cell_length_a                   7.526(3)
_cell_length_b                   11.789(4)
_cell_length_c                   30.882(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2740.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7
_cell_measurement_theta_max      14

_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    4.562
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  300
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7009
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.319
_diffrn_reflns_theta_max         27.058
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_point_group_measured_fraction_full 0.675
_reflns_number_total             3899
_reflns_number_gt                3387
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.232
_reflns_Friedel_fraction_max     0.256
_reflns_Friedel_fraction_full    0.314

_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0214P)²+1.8338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_details 
;
 Flack x determined using 695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
I1 I -0.13061(10) 0.52050(6) 0.15142(2) 0.05578(19) Uani 1 1 d . . . . .
I2 I 0.14536(9) 0.24297(8) 0.10831(2) 0.0593(2) Uani 1 1 d . . . . .
I3 I -0.22882(8) 0.23191(7) 0.17772(2) 0.05145(18) Uani 1 1 d . . . . .
I4 I -0.04953(10) 0.01204(8) -0.00946(2) 0.0652(2) Uani 1 1 d . . . . .
C1 C -0.0808(13) 0.6946(8) 0.1461(3) 0.046(3) Uani 1 1 d . . . . .
C2 C -0.0923(12) 0.7605(8) 0.1833(3) 0.044(2) Uani 1 1 d . . . . .
H2 H -0.1212 0.7271 0.2097 0.053 Uiso 1 1 calc R U . . .
C3 C -0.0207(13) 0.9243(9) 0.1442(3) 0.047(3) Uani 1 1 d . . . . .
H3 H -0.0021 1.0022 0.1439 0.057 Uiso 1 1 calc R U . . .
C4 C -0.0059(16) 0.8635(11) 0.1065(4) 0.064(3) Uani 1 1 d . . . . .
H4 H 0.0221 0.9000 0.0807 0.077 Uiso 1 1 calc R U . . .
C5 C -0.0338(12) 0.7444(12) 0.1073(3) 0.053(3) Uani 1 1 d . . . . .
H5 H -0.0208 0.7011 0.0823 0.064 Uiso 1 1 calc R U . . .
C6 C -0.0711(13) 0.9402(8) 0.2222(3) 0.043(2) Uani 1 1 d . . . . .
H6A H -0.1369 1.0096 0.2170 0.052 Uiso 1 1 calc R U . . .
H6B H -0.1343 0.8968 0.2440 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1095(13) 0.9686(9) 0.2385(3) 0.042(2) Uani 1 1 d . . . . .
C8 C 0.1902(16) 1.0695(10) 0.2263(4) 0.057(3) Uani 1 1 d . . . . .
H8 H 0.1286 1.1206 0.2089 0.068 Uiso 1 1 calc R U . . .
C9 C 0.3606(17) 1.0949(12) 0.2396(5) 0.072(4) Uani 1 1 d . . . . .
H9 H 0.4150 1.1615 0.2303 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4487(16) 1.0225(17) 0.2663(4) 0.082(4) Uani 1 1 d . . . . .
H10 H 0.5636 1.0400 0.2752 0.098 Uiso 1 1 calc R U . . .
C11 C 0.3702(19) 0.9238(13) 0.2804(4) 0.077(4) Uani 1 1 d . . . . .
H11 H 0.4310 0.8752 0.2989 0.092 Uiso 1 1 calc R U . . .
C12 C 0.2024(19) 0.8976(10) 0.2669(4) 0.061(3) Uani 1 1 d . . . . .
H12 H 0.1488 0.8314 0.2768 0.074 Uiso 1 1 calc R U . . .
C13 C 0.3663(13) 0.2545(10) 0.0670(3) 0.046(2) Uani 1 1 d . . . . .
C14 C 0.3582(13) 0.2043(9) 0.0273(3) 0.047(3) Uani 1 1 d . . . . .
H14 H 0.2558 0.1662 0.0187 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6512(14) 0.2626(11) 0.0118(4) 0.061(3) Uani 1 1 d . . . . .
H15 H 0.7481 0.2627 -0.0068 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6614(15) 0.3150(12) 0.0507(4) 0.069(4) Uani 1 1 d . . . . .
H16 H 0.7650 0.3528 0.0585 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5174(16) 0.3128(11) 0.0791(4) 0.059(3) Uani 1 1 d . . . . .
H17 H 0.5231 0.3499 0.1057 0.070 Uiso 1 1 calc R U . . .
C18 C 0.4920(18) 0.1566(11) -0.0429(4) 0.068(4) Uani 1 1 d . . . . .
H18A H 0.3813 0.1151 -0.0457 0.082 Uiso 1 1 calc R U . . .
H18B H 0.5888 0.1027 -0.0455 0.082 Uiso 1 1 calc R U . . .
C19 C 0.5054(16) 0.2431(17) -0.0796(4) 0.066(3) Uani 1 1 d . . . . .
C20 C 0.4565(19) 0.3501(16) -0.0754(5) 0.092(5) Uani 1 1 d . . . . .
H20 H 0.4141 0.3763 -0.0489 0.111 Uiso 1 1 calc R U . . .
C21 C 0.468(2) 0.4242(16) -0.1108(6) 0.106(6) Uani 1 1 d . . . . .
H21 H 0.4327 0.4994 -0.1080 0.128 Uiso 1 1 calc R U . . .
C22 C 0.534(3) 0.384(2) -0.1504(6) 0.137(11) Uani 1 1 d . . . . .
H22 H 0.5491 0.4319 -0.1741 0.164 Uiso 1 1 calc R U . . .
C23 C 0.576(3) 0.273(2) -0.1528(7) 0.133(10) Uani 1 1 d . . . . .
H23 H 0.6093 0.2434 -0.1794 0.159 Uiso 1 1 calc R U . . .
C24 C 0.5699(18) 0.2039(17) -0.1182(4) 0.094(6) Uani 1 1 d . . . . .
H24 H 0.6096 0.1294 -0.1206 0.113 Uiso 1 1 calc R U . . .
N1 N -0.0614(10) 0.8730(7) 0.1812(3) 0.0406(19) Uani 1 1 d . . . . .
N2 N 0.4991(13) 0.2102(8) 0.0004(3) 0.055(2) 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
I1 C1 2.093(10) . ?
I2 C13 2.100(10) . ?
C1 C5 1.382(14) . ?
C1 C2 1.389(13) . ?
C2 N1 1.348(12) . ?
C2 H2 0.9300 . ?
C3 N1 1.327(12) . ?
C3 C4 1.370(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.420(18) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.488(13) . ?
C6 N1 1.496(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.387(13) . ?
C7 C12 1.399(15) . ?
C8 C9 1.380(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.38(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(17) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.364(13) . ?
C13 C17 1.381(14) . ?
C14 N2 1.348(12) . ?
C14 H14 0.9300 . ?
C15 N2 1.348(13) . ?
C15 C16 1.351(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(15) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N2 1.480(13) . ?
C18 C19 1.527(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.32(2) . ?
C19 C24 1.369(17) . ?
C20 C21 1.40(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.40(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.34(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.35(2) . ?
C23 H23 0.9300 . ?
C24 H24 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
C5 C1 C2 119.8(10) . . ?
C5 C1 I1 122.0(9) . . ?
C2 C1 I1 118.2(7) . . ?
N1 C2 C1 119.9(10) . . ?
N1 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N1 C3 C4 120.7(10) . . ?
N1 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.4(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C1 C5 C4 118.2(11) . . ?
C1 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C7 C6 N1 111.2(8) . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C12 117.7(10) . . ?
C8 C7 C6 120.1(10) . . ?
C12 C7 C6 122.2(10) . . ?
C9 C8 C7 120.8(12) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.8(13) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.9(12) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.5(13) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 121.2(12) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C14 C13 C17 119.8(10) . . ?
C14 C13 I2 118.9(8) . . ?
C17 C13 I2 121.3(8) . . ?
N2 C14 C13 119.7(10) . . ?
N2 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N2 C15 C16 119.4(11) . . ?
N2 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.4(11) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C13 C17 C16 118.6(11) . . ?
C13 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
N2 C18 C19 112.5(10) . . ?
N2 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N2 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C24 120.4(18) . . ?
C20 C19 C18 123.2(13) . . ?
C24 C19 C18 116.4(17) . . ?
C19 C20 C21 120.1(18) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.5(19) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 117(2) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C22 C23 C24 123(2) . . ?
C22 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
C23 C24 C19 120(2) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C3 N1 C2 122.0(9) . . ?
C3 N1 C6 119.9(8) . . ?
C2 N1 C6 118.1(8) . . ?
C15 N2 C14 122.0(10) . . ?
C15 N2 C18 117.6(10) . . ?
C14 N2 C18 120.4(9) . . ?

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.109

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetonitrile
####################################################################### 
# 
# 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_2_NO3_PF6
_database_code_depnum_ccdc_archive 'CCDC 1476625'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1,3,5-tris(3-iodo-1-pyridiniomethyl)-2,4,6-trimethylbenzene nitrate
 hexafluorophosphate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 I3 N3, F6 P, 2(N O3)'
_chemical_formula_sum            'C27 H27 F6 I3 N5 O6 P'
_chemical_formula_weight         1043.21

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.352(2)
_cell_length_b                   13.844(3)
_cell_length_c                   14.366(3)
_cell_angle_alpha                118.339(4)
_cell_angle_beta                 101.442(4)
_cell_angle_gamma                99.631(4)
_cell_volume                     1856.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5210
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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 Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19857
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         25.223
_diffrn_reflns_theta_full        25.223
_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 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6663
_reflns_number_gt                4891
_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       'SMART (Bruker-Axs Inc)'
_computing_cell_refinement       'SAINT (Bruker-Axs Inc)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 The crystal shows positional disorder for one of the two nitrate counterions,
 resulting placed over two alternative positions half populated. 
 In the final least-squares refinement cycles, the geometries of the
 disordered nitrate counterions and those of the hexafluorophosphate ion were
 restrained to the expected ones using soft DFIX and DANG restraints.  
 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1514P)²+4.9621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         6663
_refine_ls_number_parameters     469
_refine_ls_number_restraints     122
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2561
_refine_ls_wR_factor_gt          0.2343
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
I1 I 0.10288(7) -0.34191(6) 0.19479(7) 0.0753(3) Uani 1 1 d . . . . .
I2 I 1.13287(7) 0.36550(9) 0.45977(7) 0.1035(4) Uani 1 1 d . . . . .
I3 I 0.45147(11) 0.71057(8) 0.07794(9) 0.1072(4) Uani 1 1 d . . . . .
C1 C 0.2976(8) 0.1079(8) 0.1411(7) 0.056(2) Uani 1 1 d . . . . .
C2 C 0.4258(9) 0.1130(8) 0.1570(8) 0.060(2) Uani 1 1 d . . . . .
C3 C 0.5141(7) 0.2145(8) 0.1887(7) 0.053(2) Uani 1 1 d . . . . .
C4 C 0.4759(8) 0.3110(8) 0.2064(7) 0.058(2) Uani 1 1 d . . . . .
C5 C 0.3513(8) 0.3074(8) 0.1914(7) 0.055(2) Uani 1 1 d . . . . .
C6 C 0.2582(8) 0.2040(8) 0.1581(8) 0.057(2) Uani 1 1 d . . . . .
C7 C 0.1995(10) -0.0033(9) 0.1040(9) 0.068(3) Uani 1 1 d . . . . .
H7A H 0.1166 0.0011 0.0767 0.082 Uiso 1 1 calc R U . . .
H7B H 0.2135 -0.0666 0.0425 0.082 Uiso 1 1 calc R U . . .
C8 C 0.1641(8) -0.1418(8) 0.1629(9) 0.059(2) Uani 1 1 d . . . . .
H8 H 0.1412 -0.2001 0.0884 0.071 Uiso 1 1 calc R U . . .
C9 C 0.1610(9) -0.1688(9) 0.2429(10) 0.069(3) Uani 1 1 d . . . . .
C10 C 0.1926(13) -0.0808(11) 0.3551(10) 0.086(3) Uani 1 1 d . . . . .
H10 H 0.1893 -0.0987 0.4095 0.103 Uiso 1 1 calc R U . . .
C11 C 0.2285(13) 0.0318(11) 0.3837(10) 0.091(4) Uani 1 1 d . . . . .
H11 H 0.2496 0.0909 0.4577 0.110 Uiso 1 1 calc R U . . .
C12 C 0.2333(11) 0.0577(10) 0.2999(10) 0.078(3) Uani 1 1 d . . . . .
H12 H 0.2584 0.1339 0.3186 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4629(12) 0.0068(10) 0.1398(12) 0.086(3) Uani 1 1 d . . . . .
H13A H 0.3890 -0.0540 0.1183 0.130 Uiso 1 1 calc R U . . .
H13B H 0.5016 -0.0172 0.0822 0.130 Uiso 1 1 calc R U . . .
H13C H 0.5214 0.0246 0.2081 0.130 Uiso 1 1 calc R U . . .
C14 C 0.6496(8) 0.2184(9) 0.1991(7) 0.062(2) Uani 1 1 d . . . . .
H14A H 0.6833 0.2646 0.1711 0.074 Uiso 1 1 calc R U . . .
H14B H 0.6529 0.1410 0.1525 0.074 Uiso 1 1 calc R U . . .
C15 C 0.8589(8) 0.2917(9) 0.3348(8) 0.062(2) Uani 1 1 d . . . . .
H15 H 0.8891 0.2816 0.2762 0.075 Uiso 1 1 calc R U . . .
C16 C 0.9414(10) 0.3304(10) 0.4375(9) 0.076(3) Uani 1 1 d . . . . .
C17 C 0.8949(11) 0.3441(13) 0.5236(10) 0.092(4) Uani 1 1 d . . . . .
H17 H 0.9496 0.3683 0.5933 0.111 Uiso 1 1 calc R U . . .
C18 C 0.7659(12) 0.3215(13) 0.5049(10) 0.091(4) Uani 1 1 d . . . . .
H18 H 0.7340 0.3348 0.5633 0.109 Uiso 1 1 calc R U . . .
C19 C 0.6850(10) 0.2791(11) 0.3994(9) 0.075(3) Uani 1 1 d . . . . .
H19 H 0.5982 0.2586 0.3849 0.090 Uiso 1 1 calc R U . . .
C20 C 0.5748(9) 0.4250(9) 0.2496(9) 0.068(3) Uani 1 1 d . . . . .
H20A H 0.6567 0.4141 0.2557 0.102 Uiso 1 1 calc R U . . .
H20B H 0.5558 0.4507 0.1986 0.102 Uiso 1 1 calc R U . . .
H20C H 0.5740 0.4816 0.3216 0.102 Uiso 1 1 calc R U . . .
C21 C 0.3113(9) 0.4121(8) 0.2078(8) 0.062(2) Uani 1 1 d . . . . .
H21A H 0.2288 0.4038 0.2177 0.074 Uiso 1 1 calc R U . . .
H21B H 0.3704 0.4801 0.2753 0.074 Uiso 1 1 calc R U . . .
C22 C 0.3626(10) 0.5328(9) 0.1315(9) 0.068(2) Uani 1 1 d . . . . .
H22 H 0.4084 0.5933 0.2038 0.082 Uiso 1 1 calc R U . . .
C23 C 0.3522(10) 0.5490(10) 0.0430(11) 0.073(3) Uani 1 1 d . . . . .
C24 C 0.2849(11) 0.4619(11) -0.0638(11) 0.082(3) Uani 1 1 d . . . . .
H24 H 0.2788 0.4729 -0.1234 0.099 Uiso 1 1 calc R U . . .
C25 C 0.2260(12) 0.3565(12) -0.0802(11) 0.086(3) Uani 1 1 d . . . . .
H25 H 0.1786 0.2957 -0.1518 0.103 Uiso 1 1 calc R U . . .
C26 C 0.2370(9) 0.3406(10) 0.0089(9) 0.071(3) Uani 1 1 d . . . . .
H26 H 0.1972 0.2695 -0.0027 0.085 Uiso 1 1 calc R U . . .
C27 C 0.1197(9) 0.1961(11) 0.1408(11) 0.083(3) Uani 1 1 d . . . . .
H27A H 0.1087 0.2688 0.1558 0.125 Uiso 1 1 calc R U . . .
H27B H 0.0710 0.1374 0.0651 0.125 Uiso 1 1 calc R U . . .
H27C H 0.0919 0.1771 0.1906 0.125 Uiso 1 1 calc R U . . .
N1 N 0.2011(7) -0.0289(6) 0.1929(6) 0.0559(17) Uani 1 1 d . . . . .
N2 N 0.7332(7) 0.2681(8) 0.3186(6) 0.0607(19) Uani 1 1 d . . . . .
N3 N 0.3057(7) 0.4286(7) 0.1124(6) 0.0593(18) Uani 1 1 d . . . . .
N4 N -0.0745(7) -0.6146(7) 0.1455(7) 0.0576(18) Uani 1 1 d . . . . .
O1 O -0.1381(10) -0.7175(8) 0.0956(7) 0.104(3) Uani 1 1 d . . . . .
O2 O -0.1096(11) -0.5445(9) 0.2189(9) 0.112(3) Uani 1 1 d . . . . .
O3 O 0.0156(11) -0.5871(10) 0.1215(12) 0.131(4) Uani 1 1 d . . . . .
F1 F 0.9682(10) 1.0728(10) 0.2877(11) 0.240(7) Uani 1 1 d D U . . .
F2 F 0.8556(18) 0.9083(14) 0.2546(15) 0.280(7) Uani 1 1 d D U . . .
F3 F 0.7157(8) 0.8935(9) 0.1189(11) 0.215(6) Uani 1 1 d D U . . .
F4 F 0.8271(12) 1.0518(9) 0.1447(10) 0.178(4) Uani 1 1 d D U . . .
F5 F 0.9143(9) 0.9187(8) 0.1258(11) 0.194(5) Uani 1 1 d D U . . .
F6 F 0.7743(13) 1.0468(12) 0.2828(11) 0.210(5) Uani 1 1 d D U . . .
P1 P 0.8424(5) 0.9828(4) 0.2003(6) 0.154(2) Uani 1 1 d D U . . .
N5A N 1.4512(9) 0.4108(11) 0.4767(10) 0.063(4) Uani 0.5 1 d D U P A 1
O4A O 1.4024(11) 0.3123(10) 0.4484(12) 0.068(3) Uani 0.5 1 d D U P A 1
O5A O 1.3895(17) 0.4662(14) 0.4533(19) 0.116(8) Uani 0.5 1 d D U P A 1
O6A O 1.5668(11) 0.4561(16) 0.521(2) 0.134(10) Uani 0.5 1 d D U P A 1
N5B N 1.533(4) 0.185(3) 0.580(2) 0.251(16) Uani 0.5 1 d D U P B 2
O4B O 1.513(3) 0.279(2) 0.6151(15) 0.146(10) Uani 0.5 1 d D U P B 2
O5B O 1.531(4) 0.128(3) 0.482(2) 0.297(19) Uani 0.5 1 d D U P B 2
O6B O 1.525(5) 0.135(3) 0.631(3) 0.30(2) Uani 0.5 1 d D U P B 2


_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
I1 C9 2.092(10) . ?
I2 C16 2.071(11) . ?
I3 C23 2.095(11) . ?
C1 C6 1.402(13) . ?
C1 C2 1.412(13) . ?
C1 C7 1.519(12) . ?
C2 C3 1.389(12) . ?
C2 C13 1.517(14) . ?
C3 C4 1.397(13) . ?
C3 C14 1.505(12) . ?
C4 C5 1.377(12) . ?
C4 C20 1.529(12) . ?
C5 C6 1.427(12) . ?
C5 C21 1.517(13) . ?
C6 C27 1.519(13) . ?
C7 N1 1.476(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.368(11) . ?
C8 C9 1.372(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.404(16) . ?
C10 C11 1.370(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(17) . ?
C11 H11 0.9300 . ?
C12 N1 1.347(14) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.529(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N2 1.355(12) . ?
C15 C16 1.369(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(17) . ?
C17 C18 1.387(17) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(15) . ?
C18 H18 0.9300 . ?
C19 N2 1.334(13) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N3 1.484(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.347(12) . ?
C22 C23 1.379(15) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(17) . ?
C24 C25 1.384(17) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(16) . ?
C25 H25 0.9300 . ?
C26 N3 1.344(13) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N4 O3 1.201(12) . ?
N4 O2 1.240(13) . ?
N4 O1 1.243(11) . ?
F1 P1 1.542(8) . ?
F2 P1 1.570(8) . ?
F3 P1 1.526(8) . ?
F4 P1 1.518(8) . ?
F5 P1 1.512(8) . ?
F6 P1 1.545(8) . ?
N5A O4A 1.210(8) . ?
N5A O5A 1.234(9) . ?
N5A O6A 1.239(8) . ?
N5B O4B 1.230(10) . ?
N5B O6B 1.233(10) . ?
N5B O5B 1.238(10) . ?

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
C6 C1 C2 121.2(8) . . ?
C6 C1 C7 118.8(8) . . ?
C2 C1 C7 120.0(9) . . ?
C3 C2 C1 119.4(8) . . ?
C3 C2 C13 122.0(9) . . ?
C1 C2 C13 118.6(9) . . ?
C2 C3 C4 119.9(8) . . ?
C2 C3 C14 119.7(9) . . ?
C4 C3 C14 120.4(8) . . ?
C5 C4 C3 121.4(8) . . ?
C5 C4 C20 119.0(9) . . ?
C3 C4 C20 119.6(8) . . ?
C4 C5 C6 120.1(8) . . ?
C4 C5 C21 120.5(8) . . ?
C6 C5 C21 119.4(8) . . ?
C1 C6 C5 118.1(8) . . ?
C1 C6 C27 120.0(8) . . ?
C5 C6 C27 121.9(9) . . ?
N1 C7 C1 114.0(8) . . ?
N1 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C9 119.9(9) . . ?
N1 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.1(10) . . ?
C8 C9 I1 119.2(8) . . ?
C10 C9 I1 120.7(8) . . ?
C11 C10 C9 119.3(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.7(11) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N1 C12 C11 119.4(10) . . ?
N1 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 N2 113.6(7) . . ?
C3 C14 H14A 108.8 . . ?
N2 C14 H14A 108.8 . . ?
C3 C14 H14B 108.8 . . ?
N2 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
N2 C15 C16 120.0(9) . . ?
N2 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.3(10) . . ?
C15 C16 I2 119.1(8) . . ?
C17 C16 I2 121.6(8) . . ?
C16 C17 C18 119.3(10) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 119.9(11) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N2 C19 C18 119.1(10) . . ?
N2 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C5 112.6(8) . . ?
N3 C21 H21A 109.1 . . ?
C5 C21 H21A 109.1 . . ?
N3 C21 H21B 109.1 . . ?
C5 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
N3 C22 C23 119.5(10) . . ?
N3 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 121.5(10) . . ?
C24 C23 I3 121.2(8) . . ?
C22 C23 I3 117.3(9) . . ?
C23 C24 C25 117.5(10) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
C24 C25 C26 120.8(12) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
N3 C26 C25 119.5(11) . . ?
N3 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C6 C27 H27A 109.5 . . ?
C6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 N1 C8 121.6(8) . . ?
C12 N1 C7 120.0(8) . . ?
C8 N1 C7 118.3(8) . . ?
C19 N2 C15 122.3(8) . . ?
C19 N2 C14 122.1(8) . . ?
C15 N2 C14 115.4(8) . . ?
C26 N3 C22 121.3(9) . . ?
C26 N3 C21 118.9(8) . . ?
C22 N3 C21 119.7(8) . . ?
O3 N4 O2 123.2(10) . . ?
O3 N4 O1 120.2(11) . . ?
O2 N4 O1 116.6(9) . . ?
F5 P1 F4 91.2(7) . . ?
F5 P1 F3 92.7(6) . . ?
F4 P1 F3 90.2(7) . . ?
F5 P1 F1 89.5(7) . . ?
F4 P1 F1 92.0(7) . . ?
F3 P1 F1 176.9(9) . . ?
F5 P1 F6 175.9(9) . . ?
F4 P1 F6 92.4(7) . . ?
F3 P1 F6 89.3(7) . . ?
F1 P1 F6 88.4(7) . . ?
F5 P1 F2 88.2(8) . . ?
F4 P1 F2 178.4(9) . . ?
F3 P1 F2 88.3(8) . . ?
F1 P1 F2 89.6(8) . . ?
F6 P1 F2 88.2(10) . . ?
O4A N5A O5A 121.2(9) . . ?
O4A N5A O6A 121.0(9) . . ?
O5A N5A O6A 117.5(9) . . ?
O4B N5B O6B 119.6(13) . . ?
O4B N5B O5B 119.9(13) . . ?
O6B N5B O5B 118.0(12) . . ?

_refine_diff_density_max         1.605
_refine_diff_density_min         -1.139
_refine_diff_density_rms         0.184

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetonitrile
####################################################################### 
# 
# 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_2_BR_PF6
_database_code_depnum_ccdc_archive 'CCDC 1476626'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
;
1,3,5-tris(3-iodo-1-pyridiniomethyl)-2,4,6-trimethylbenzene bromide 
 hexafluorophosphate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 I3 N3, 2(F6 P), Br'
_chemical_formula_sum            'C27 H27 Br F12 I3 N3 P2'
_chemical_formula_weight         1144.06

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'
Br Br -0.2901 2.4595 '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'
I I -0.4742 1.8119 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   24.1628(19)
_cell_length_b                   11.4413(9)
_cell_length_c                   27.559(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.9772(14)
_cell_angle_gamma                90
_cell_volume                     7545.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6343
_cell_measurement_theta_min      2
_cell_measurement_theta_max      21

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_F_000             4336
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_process_details   'Sadabs (Krause et al., 2015)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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 Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31513
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.492
_diffrn_reflns_theta_max         25.053
_diffrn_reflns_theta_full        25.053
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6669
_reflns_number_gt                4435
_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       'SMART (Bruker-Axs Inc)'
_computing_cell_refinement       'SAINT (Bruker-Axs Inc)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1135P)²+32.2693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         6669
_refine_ls_number_parameters     436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.2127
_refine_ls_wR_factor_gt          0.1877
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.003
_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
C1 C 0.5405(4) 0.2339(7) 0.5680(3) 0.064(2) Uani 1 1 d . . . . .
C2 C 0.5454(4) 0.3539(7) 0.5755(3) 0.065(2) Uani 1 1 d . . . . .
C3 C 0.5123(4) 0.4093(7) 0.6062(3) 0.064(2) Uani 1 1 d . . . . .
C4 C 0.4768(3) 0.3431(7) 0.6321(3) 0.0604(19) Uani 1 1 d . . . . .
C5 C 0.4737(3) 0.2223(7) 0.6256(3) 0.0571(18) Uani 1 1 d . . . . .
C6 C 0.5035(3) 0.1680(7) 0.5921(3) 0.0584(18) Uani 1 1 d . . . . .
C7 C 0.5762(4) 0.1752(8) 0.5349(3) 0.072(2) Uani 1 1 d . . . . .
H7A H 0.5578 0.1042 0.5221 0.086 Uiso 1 1 calc R U . . .
H7B H 0.5795 0.2264 0.5074 0.086 Uiso 1 1 calc R U . . .
C8 C 0.6715(5) 0.1093(8) 0.5307(4) 0.084(3) Uani 1 1 d . . . . .
H8 H 0.6617 0.1057 0.4969 0.100 Uiso 1 1 calc R U . . .
C9 C 0.7237(5) 0.0786(10) 0.5511(5) 0.103(4) Uani 1 1 d . . . . .
C10 C 0.7396(5) 0.0839(12) 0.6008(6) 0.114(4) Uani 1 1 d . . . . .
H10 H 0.7756 0.0635 0.6146 0.136 Uiso 1 1 calc R U . . .
C11 C 0.7004(5) 0.1205(12) 0.6299(5) 0.104(4) Uani 1 1 d . . . . .
H11 H 0.7096 0.1245 0.6638 0.125 Uiso 1 1 calc R U . . .
C12 C 0.6472(4) 0.1511(9) 0.6075(3) 0.083(3) Uani 1 1 d . . . . .
H12 H 0.6208 0.1761 0.6267 0.099 Uiso 1 1 calc R U . . .
C13 C 0.5869(5) 0.4232(9) 0.5511(5) 0.105(4) Uani 1 1 d . . . . .
H13A H 0.6142 0.3712 0.5407 0.157 Uiso 1 1 calc R U . . .
H13B H 0.6052 0.4790 0.5739 0.157 Uiso 1 1 calc R U . . .
H13C H 0.5677 0.4635 0.5231 0.157 Uiso 1 1 calc R U . . .
C14 C 0.5122(4) 0.5417(7) 0.6103(3) 0.068(2) Uani 1 1 d . . . . .
H14A H 0.5262 0.5741 0.5819 0.081 Uiso 1 1 calc R U . . .
H14B H 0.4738 0.5676 0.6094 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5473(4) 0.7079(7) 0.6603(3) 0.064(2) Uani 1 1 d . . . . .
H15 H 0.5283 0.7552 0.6361 0.077 Uiso 1 1 calc R U . . .
C16 C 0.5773(4) 0.7577(7) 0.7016(3) 0.067(2) Uani 1 1 d . . . . .
C17 C 0.6036(4) 0.6885(8) 0.7369(3) 0.077(2) Uani 1 1 d . . . . .
H17 H 0.6227 0.7214 0.7653 0.092 Uiso 1 1 calc R U . . .
C18 C 0.6023(4) 0.5689(8) 0.7311(4) 0.078(2) Uani 1 1 d . . . . .
H18 H 0.6213 0.5209 0.7551 0.093 Uiso 1 1 calc R U . . .
C19 C 0.5730(4) 0.5209(8) 0.6897(3) 0.072(2) Uani 1 1 d . . . . .
H19 H 0.5719 0.4402 0.6856 0.087 Uiso 1 1 calc R U . . .
C20 C 0.4445(5) 0.4026(8) 0.6682(4) 0.083(3) Uani 1 1 d . . . . .
H20A H 0.4092 0.3643 0.6680 0.125 Uiso 1 1 calc R U . . .
H20B H 0.4385 0.4830 0.6590 0.125 Uiso 1 1 calc R U . . .
H20C H 0.4654 0.3983 0.7004 0.125 Uiso 1 1 calc R U . . .
C21 C 0.4396(3) 0.1525(7) 0.6572(3) 0.0582(18) Uani 1 1 d . . . . .
H21A H 0.4533 0.0727 0.6589 0.070 Uiso 1 1 calc R U . . .
H21B H 0.4456 0.1844 0.6901 0.070 Uiso 1 1 calc R U . . .
C22 C 0.3470(4) 0.0911(8) 0.6681(3) 0.070(2) Uani 1 1 d . . . . .
H22 H 0.3637 0.0532 0.6962 0.083 Uiso 1 1 calc R U . . .
C23 C 0.2903(4) 0.0866(10) 0.6554(4) 0.087(3) Uani 1 1 d . . . . .
C24 C 0.2660(4) 0.1459(12) 0.6149(4) 0.103(4) Uani 1 1 d . . . . .
H24 H 0.2273 0.1472 0.6068 0.124 Uiso 1 1 calc R U . . .
C25 C 0.2991(5) 0.2026(11) 0.5867(4) 0.102(4) Uani 1 1 d . . . . .
H25 H 0.2830 0.2401 0.5583 0.123 Uiso 1 1 calc R U . . .
C26 C 0.3555(4) 0.2056(8) 0.5993(3) 0.073(2) Uani 1 1 d . . . . .
H26 H 0.3778 0.2455 0.5800 0.088 Uiso 1 1 calc R U . . .
C27 C 0.4962(4) 0.0375(7) 0.5812(3) 0.071(2) Uani 1 1 d . . . . .
H27A H 0.4644 0.0088 0.5949 0.106 Uiso 1 1 calc R U . . .
H27B H 0.5291 -0.0038 0.5954 0.106 Uiso 1 1 calc R U . . .
H27C H 0.4905 0.0255 0.5464 0.106 Uiso 1 1 calc R U . . .
Br1 Br 0.60668(7) 1.22944(9) 0.72270(4) 0.1140(5) Uani 1 1 d . . . . .
I1 I 0.78012(4) 0.01607(10) 0.50659(5) 0.1511(5) Uani 1 1 d . . . . .
I2 I 0.58120(3) 0.94147(5) 0.70721(2) 0.0831(3) Uani 1 1 d . . . . .
I3 I 0.24301(4) -0.01030(13) 0.69920(5) 0.1706(6) Uani 1 1 d . . . . .
N1 N 0.6336(3) 0.1452(6) 0.5595(2) 0.0677(18) Uani 1 1 d . . . . .
N2 N 0.5458(3) 0.5907(5) 0.6552(2) 0.0589(16) Uani 1 1 d . . . . .
N3 N 0.3785(2) 0.1502(5) 0.6400(2) 0.0549(14) Uani 1 1 d . . . . .
F1 F 0.9194(5) 0.3417(11) 0.6560(3) 0.186(5) Uani 1 1 d . . . . .
F2 F 0.8708(4) 0.4127(6) 0.5922(3) 0.135(3) Uani 1 1 d . . . . .
F3 F 0.8331(4) 0.3054(11) 0.6497(4) 0.185(4) Uani 1 1 d . . . . .
F4 F 0.8885(6) 0.1645(8) 0.6386(4) 0.212(6) Uani 1 1 d . . . . .
F5 F 0.9298(3) 0.2688(7) 0.5845(3) 0.128(3) Uani 1 1 d . . . . .
F6 F 0.8357(5) 0.2459(9) 0.5735(4) 0.202(5) Uani 1 1 d . . . . .
P1 P 0.88015(12) 0.2830(2) 0.61641(10) 0.0832(7) Uani 1 1 d . . . . .
F7 F 0.6217(3) -0.1193(6) 0.5826(2) 0.109(2) Uani 1 1 d . . . . .
F8 F 0.5510(2) -0.2251(6) 0.5462(2) 0.0971(17) Uani 1 1 d . . . . .
F9 F 0.6282(2) -0.3137(5) 0.5823(2) 0.0921(16) Uani 1 1 d . . . . .
F10 F 0.6795(2) -0.2048(6) 0.5370(3) 0.118(2) Uani 1 1 d . . . . .
F11 F 0.6029(3) -0.1147(5) 0.5014(2) 0.0951(16) Uani 1 1 d . . . . .
F12 F 0.6076(3) -0.3092(5) 0.4997(2) 0.111(2) Uani 1 1 d . . . . .
P2 P 0.61529(10) -0.21425(18) 0.54143(8) 0.0632(5) 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
C1 C2 1.391(11) . ?
C1 C6 1.405(11) . ?
C1 C7 1.498(11) . ?
C2 C3 1.395(11) . ?
C2 C13 1.508(12) . ?
C3 C4 1.410(11) . ?
C3 C14 1.519(11) . ?
C4 C5 1.394(11) . ?
C4 C20 1.508(11) . ?
C5 C6 1.392(10) . ?
C5 C21 1.509(10) . ?
C6 C27 1.529(11) . ?
C7 N1 1.496(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.355(17) . ?
C8 N1 1.357(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(18) . ?
C9 I1 2.083(10) . ?
C10 C11 1.388(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(15) . ?
C11 H11 0.9300 . ?
C12 N1 1.319(11) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.492(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N2 1.347(10) . ?
C15 C16 1.383(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.345(12) . ?
C16 I2 2.110(8) . ?
C17 C18 1.378(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(14) . ?
C18 H18 0.9300 . ?
C19 N2 1.342(11) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N3 1.485(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.341(10) . ?
C22 C23 1.367(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(15) . ?
C23 I3 2.091(10) . ?
C24 C25 1.356(15) . ?
C24 H24 0.9300 . ?
C25 C26 1.360(14) . ?
C25 H25 0.9300 . ?
C26 N3 1.340(10) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
F1 P1 1.502(9) . ?
F2 P1 1.631(8) . ?
F3 P1 1.576(8) . ?
F4 P1 1.489(8) . ?
F5 P1 1.590(7) . ?
F6 P1 1.543(10) . ?
F7 P2 1.564(6) . ?
F8 P2 1.581(6) . ?
F9 P2 1.600(6) . ?
F10 P2 1.577(6) . ?
F11 P2 1.585(6) . ?
F12 P2 1.573(6) . ?

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 C1 C6 120.4(7) . . ?
C2 C1 C7 119.2(7) . . ?
C6 C1 C7 120.4(7) . . ?
C1 C2 C3 119.6(7) . . ?
C1 C2 C13 120.1(8) . . ?
C3 C2 C13 120.3(8) . . ?
C2 C3 C4 120.2(7) . . ?
C2 C3 C14 120.4(7) . . ?
C4 C3 C14 119.3(7) . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 C20 120.6(7) . . ?
C3 C4 C20 119.8(7) . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 C21 121.3(7) . . ?
C4 C5 C21 118.3(7) . . ?
C5 C6 C1 119.7(7) . . ?
C5 C6 C27 120.7(7) . . ?
C1 C6 C27 119.6(7) . . ?
N1 C7 C1 113.7(7) . . ?
N1 C7 H7A 108.8 . . ?
C1 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 N1 120.1(10) . . ?
C9 C8 H8 119.9 . . ?
N1 C8 H8 119.9 . . ?
C8 C9 C10 121.2(10) . . ?
C8 C9 I1 119.5(10) . . ?
C10 C9 I1 119.3(10) . . ?
C9 C10 C11 118.3(13) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C12 118.7(12) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N1 C12 C11 121.3(9) . . ?
N1 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C3 115.5(7) . . ?
N2 C14 H14A 108.4 . . ?
C3 C14 H14A 108.4 . . ?
N2 C14 H14B 108.4 . . ?
C3 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
N2 C15 C16 119.9(8) . . ?
N2 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.7(8) . . ?
C17 C16 I2 121.4(7) . . ?
C15 C16 I2 119.0(6) . . ?
C16 C17 C18 119.9(9) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.7(9) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N2 C19 C18 119.8(8) . . ?
N2 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C5 115.1(6) . . ?
N3 C21 H21A 108.5 . . ?
C5 C21 H21A 108.5 . . ?
N3 C21 H21B 108.5 . . ?
C5 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
N3 C22 C23 120.1(8) . . ?
N3 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.4(9) . . ?
C24 C23 I3 121.8(8) . . ?
C22 C23 I3 118.8(7) . . ?
C25 C24 C23 119.0(10) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 121.0(10) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
N3 C26 C25 119.1(9) . . ?
N3 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C6 C27 H27A 109.5 . . ?
C6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 N1 C8 120.4(9) . . ?
C12 N1 C7 122.0(7) . . ?
C8 N1 C7 117.6(8) . . ?
C19 N2 C15 121.0(7) . . ?
C19 N2 C14 121.3(7) . . ?
C15 N2 C14 117.6(7) . . ?
C26 N3 C22 121.2(7) . . ?
C26 N3 C21 122.4(7) . . ?
C22 N3 C21 116.4(6) . . ?
F4 P1 F1 94.1(8) . . ?
F4 P1 F6 96.1(7) . . ?
F1 P1 F6 169.3(7) . . ?
F4 P1 F3 88.7(6) . . ?
F1 P1 F3 86.5(6) . . ?
F6 P1 F3 90.5(7) . . ?
F4 P1 F5 93.7(5) . . ?
F1 P1 F5 89.9(6) . . ?
F6 P1 F5 92.7(6) . . ?
F3 P1 F5 175.8(6) . . ?
F4 P1 F2 179.9(6) . . ?
F1 P1 F2 85.9(6) . . ?
F6 P1 F2 83.9(5) . . ?
F3 P1 F2 91.2(6) . . ?
F5 P1 F2 86.5(4) . . ?
F7 P2 F12 179.0(4) . . ?
F7 P2 F10 90.5(4) . . ?
F12 P2 F10 90.5(4) . . ?
F7 P2 F8 89.7(4) . . ?
F12 P2 F8 89.4(4) . . ?
F10 P2 F8 179.3(4) . . ?
F7 P2 F11 89.8(4) . . ?
F12 P2 F11 89.8(3) . . ?
F10 P2 F11 89.4(3) . . ?
F8 P2 F11 91.2(3) . . ?
F7 P2 F9 89.6(4) . . ?
F12 P2 F9 90.8(3) . . ?
F10 P2 F9 90.3(3) . . ?
F8 P2 F9 89.1(3) . . ?
F11 P2 F9 179.3(4) . . ?

_refine_diff_density_max         1.945
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.124




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetonitrile
