# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_150715_bispy_2bz
_database_code_depnum_ccdc_archive 'CCDC 1423659'
_audit_update_record             
;
2015-09-11 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
N,N'-bisbenzyl-1,4-bis(4-pyridin-1-iumylethynyl)benzenebishexafluorophosphate
_chemical_formula_moiety         '2(F6 P), C34 H26 N2, 2(C2 H3 N)'
_chemical_formula_sum            'C38 H32 F12 N4 P2'
_chemical_formula_weight         834.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 B2 Si8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.8259(14)
_cell_length_b                   9.7216(8)
_cell_length_c                   12.7688(13)
_cell_angle_alpha                104.695(8)
_cell_angle_beta                 100.791(11)
_cell_angle_gamma                108.868(11)
_cell_volume                     958.4(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3846
_cell_measurement_theta_min      3.1852
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6002
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0305018000
_diffrn_orient_matrix_UB_12      -0.0014689000
_diffrn_orient_matrix_UB_13      0.0550270000
_diffrn_orient_matrix_UB_21      0.0745068000
_diffrn_orient_matrix_UB_22      -0.0025910000
_diffrn_orient_matrix_UB_23      -0.0120127000
_diffrn_orient_matrix_UB_31      0.0376123000
_diffrn_orient_matrix_UB_32      0.0818728000
_diffrn_orient_matrix_UB_33      0.0209322000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2254
_reflns_number_total             3498
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.013(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.394
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.1090
_refine_ls_restrained_S_all      1.394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3342
_refine_ls_wR_factor_ref         0.3863
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C1(H1), C17(H17), C9(H9), C12(H12), C16(H16), C5(H5),
 C11(H11), C8(H8)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
P1 P 0.3520(2) -0.04374(16) 0.69464(13) 0.0701(7) Uani 1 d . . .
F1 F 0.4843(10) 0.1117(7) 0.7133(9) 0.216(4) Uani 1 d . . .
F3 F 0.2198(8) -0.1906(5) 0.6936(10) 0.247(5) Uani 1 d . . .
F4 F 0.4892(7) -0.1090(8) 0.7165(7) 0.179(3) Uani 1 d . . .
F2 F 0.2212(9) 0.0187(9) 0.6604(9) 0.227(4) Uani 1 d . . .
F5 F 0.3508(19) 0.0280(11) 0.8091(6) 0.311(7) Uani 1 d . . .
N1 N 0.4070(5) 0.4889(4) 0.6788(3) 0.0468(10) Uani 1 d . . .
C4 C 0.2172(7) 0.3514(6) 0.9391(5) 0.0660(15) Uani 1 d . . .
H4 H 0.1726 0.2487 0.9348 0.079 Uiso 1 calc . . R
C3 C 0.1878(7) 0.4601(8) 1.0156(4) 0.0721(16) Uani 1 d . . .
H3 H 0.1246 0.4324 1.0631 0.086 Uiso 1 calc . . R
C2 C 0.2539(8) 0.6100(7) 1.0198(5) 0.0729(16) Uani 1 d . . .
H2 H 0.2367 0.6857 1.0717 0.087 Uiso 1 calc . . R
C15 C 0.0702(6) 0.0806(5) 0.1159(3) 0.0435(11) Uani 1 d . . .
C6 C 0.3759(6) 0.5403(5) 0.8718(3) 0.0465(11) Uani 1 d . . .
C10 C 0.2668(6) 0.3132(5) 0.4526(4) 0.0484(12) Uani 1 d . . .
C1 C 0.3463(7) 0.6508(6) 0.9478(4) 0.0624(14) Uani 1 d . . .
H1 H 0.3886 0.7530 0.9506 0.075 Uiso 1 calc . . R
C17 C 0.1468(6) -0.0046(5) 0.0572(4) 0.0490(12) Uani 1 d . . .
H17 H 0.2454 -0.0075 0.0959 0.059 Uiso 1 calc . . R
C9 C 0.1969(6) 0.4068(6) 0.5084(4) 0.0546(13) Uani 1 d . . .
H9 H 0.0995 0.4106 0.4686 0.065 Uiso 1 calc . . R
C12 C 0.4756(6) 0.3966(6) 0.6279(4) 0.0549(12) Uani 1 d . . .
H12 H 0.5717 0.3934 0.6700 0.066 Uiso 1 calc . . R
C16 C -0.0781(6) 0.0847(5) 0.0577(4) 0.0511(12) Uani 1 d . . .
H16 H -0.1303 0.1411 0.0961 0.061 Uiso 1 calc . . R
C5 C 0.3102(7) 0.3905(5) 0.8695(4) 0.0559(13) Uani 1 d . . .
H5 H 0.3296 0.3145 0.8196 0.067 Uiso 1 calc . . R
C11 C 0.4089(7) 0.3075(6) 0.5165(4) 0.0552(13) Uani 1 d . . .
H11 H 0.4581 0.2434 0.4835 0.066 Uiso 1 calc . . R
C7 C 0.4831(7) 0.5883(6) 0.7983(4) 0.0584(13) Uani 1 d . . .
H7A H 0.5014 0.6941 0.8039 0.070 Uiso 1 calc . . R
H7B H 0.5914 0.5847 0.8260 0.070 Uiso 1 calc . . R
C8 C 0.2661(6) 0.4919(5) 0.6181(4) 0.0546(13) Uani 1 d . . .
H8 H 0.2164 0.5541 0.6531 0.066 Uiso 1 calc . . R
C14 C 0.1413(6) 0.1626(5) 0.2339(4) 0.0513(12) Uani 1 d . . .
C13 C 0.2008(6) 0.2316(5) 0.3348(3) 0.0491(12) Uani 1 d . . .
C18 C -0.1163(8) 0.3064(8) 0.6853(5) 0.0760(17) Uani 1 d . . .
N2 N -0.1124(9) 0.4269(8) 0.6995(6) 0.113(2) Uani 1 d . . .
C19 C -0.1192(12) 0.1556(8) 0.6657(7) 0.114(3) Uani 1 d . . .
H19A H -0.1984 0.1005 0.6979 0.171 Uiso 1 calc . . GR
H19B H -0.0098 0.1616 0.7003 0.171 Uiso 1 calc . . GR
H19C H -0.1515 0.1022 0.5857 0.171 Uiso 1 calc . . GR
F6 F 0.3426(18) -0.1177(17) 0.5792(5) 0.326(8) Uani 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
P1 F1 1.509(6) . ?
P1 F3 1.519(6) . ?
P1 F4 1.551(5) . ?
P1 F2 1.514(6) . ?
P1 F5 1.455(6) . ?
P1 F6 1.440(6) . ?
N1 C12 1.340(6) . ?
N1 C7 1.470(5) . ?
N1 C8 1.350(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.373(8) . ?
C4 C5 1.360(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.365(9) . ?
C2 H2 0.9300 . ?
C2 C1 1.388(8) . ?
C15 C17 1.393(6) . ?
C15 C16 1.397(7) . ?
C15 C14 1.418(6) . ?
C6 C1 1.382(7) . ?
C6 C5 1.373(6) . ?
C6 C7 1.504(7) . ?
C10 C9 1.384(6) . ?
C10 C11 1.388(7) . ?
C10 C13 1.414(6) . ?
C1 H1 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.382(6) 2 ?
C9 H9 0.9300 . ?
C9 C8 1.336(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.361(7) . ?
C16 C17 1.382(6) 2 ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C14 C13 1.211(6) . ?
C18 N2 1.128(8) . ?
C18 C19 1.414(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
F1 P1 F3 171.7(5) . . ?
F1 P1 F4 90.4(4) . . ?
F1 P1 F2 88.0(4) . . ?
F3 P1 F4 90.7(4) . . ?
F2 P1 F3 91.8(5) . . ?
F2 P1 F4 173.5(5) . . ?
F5 P1 F1 84.5(5) . . ?
F5 P1 F3 87.2(6) . . ?
F5 P1 F4 102.0(8) . . ?
F5 P1 F2 84.1(8) . . ?
F6 P1 F1 97.6(8) . . ?
F6 P1 F3 90.7(8) . . ?
F6 P1 F4 80.7(5) . . ?
F6 P1 F2 93.3(5) . . ?
F6 P1 F5 176.6(8) . . ?
C12 N1 C7 121.5(4) . . ?
C12 N1 C8 119.0(4) . . ?
C8 N1 C7 119.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C5 C4 C3 121.6(5) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 C4 118.1(5) . . ?
C2 C3 H3 120.9 . . ?
C3 C2 H2 119.6 . . ?
C3 C2 C1 120.8(5) . . ?
C1 C2 H2 119.6 . . ?
C17 C15 C16 119.5(4) . . ?
C17 C15 C14 120.6(4) . . ?
C16 C15 C14 119.9(4) . . ?
C1 C6 C7 119.5(4) . . ?
C5 C6 C1 118.1(5) . . ?
C5 C6 C7 122.4(4) . . ?
C9 C10 C11 117.1(4) . . ?
C9 C10 C13 121.7(4) . . ?
C11 C10 C13 121.2(4) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 C2 120.4(5) . . ?
C6 C1 H1 119.8 . . ?
C15 C17 H17 119.6 . . ?
C16 C17 C15 120.8(4) 2 . ?
C16 C17 H17 119.6 2 . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.5(5) . . ?
C8 C9 H9 119.2 . . ?
N1 C12 H12 119.0 . . ?
N1 C12 C11 122.0(4) . . ?
C11 C12 H12 119.0 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(4) 2 . ?
C17 C16 H16 120.2 2 . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
N1 C7 C6 112.5(4) . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 H8 119.5 . . ?
C9 C8 N1 120.9(4) . . ?
C9 C8 H8 119.5 . . ?
C13 C14 C15 179.3(5) . . ?
C14 C13 C10 178.6(5) . . ?
N2 C18 C19 178.7(9) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
N1 C12 C11 C10 0.9(8) . . . . ?
C4 C3 C2 C1 0.9(9) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
C3 C2 C1 C6 -1.3(8) . . . . ?
C15 C14 C13 C10 -69(56) . . . . ?
C10 C9 C8 N1 -0.3(8) . . . . ?
C1 C6 C5 C4 0.7(7) . . . . ?
C1 C6 C7 N1 -132.6(5) . . . . ?
C17 C15 C16 C17 -0.1(7) . . . 2 ?
C17 C15 C14 C13 -109(49) . . . . ?
C9 C10 C11 C12 -2.4(7) . . . . ?
C9 C10 C13 C14 -7(21) . . . . ?
C12 N1 C7 C6 -113.4(5) . . . . ?
C12 N1 C8 C9 -1.3(7) . . . . ?
C16 C15 C17 C16 0.1(7) . . . 2 ?
C16 C15 C14 C13 70(49) . . . . ?
C5 C4 C3 C2 0.4(8) . . . . ?
C5 C6 C1 C2 0.5(7) . . . . ?
C5 C6 C7 N1 49.8(6) . . . . ?
C11 C10 C9 C8 2.1(8) . . . . ?
C11 C10 C13 C14 175(100) . . . . ?
C7 N1 C12 C11 -178.1(4) . . . . ?
C7 N1 C8 C9 177.8(4) . . . . ?
C7 C6 C1 C2 -177.1(5) . . . . ?
C7 C6 C5 C4 178.3(5) . . . . ?
C8 N1 C12 C11 1.0(7) . . . . ?
C8 N1 C7 C6 67.6(6) . . . . ?
C14 C15 C17 C16 180.0(4) . . . 2 ?
C14 C15 C16 C17 -180.0(4) . . . 2 ?
C13 C10 C9 C8 -175.4(4) . . . . ?
C13 C10 C11 C12 175.2(4) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
